


Cassie

by Certeis



Category: Original Work
Genre: BDSM, Crossdressing, F/F, Forced Feminization, Futanari, Incest, Mind Games, Mommy Issues, Multi, Other, Rape/Non-con Elements, Twinks
Language: English
Status: Completed
Published: 2019-12-15
Updated: 2020-07-20
Packaged: 2021-02-25 21:27:54
Rating: Not Rated
Warnings: Rape/Non-Con
Chapters: 2
Words: 26,405
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21812185
Author URL: https://archiveofourown.org/users/Certeis/pseuds/Certeis
Summary: Casper, tired of arguing with his strict, puritanical mother Cassandra, reconnects with his estranged mother, the inappropriate, flirty, slightly-too-affectionate Evelynn.  He soon discovers the reason why they're estranged... as Evelynn goes about making Casper into her perfect baby girl, Cassie.A collab with a friend of mine ^^
Comments: 13
Kudos: 118





	1. She's just kind of inappropriate

Casper wandered up his driveway, a bit of a wobble in his step and a goofy smile on his face. It was late, way past his curfew. He paused as he approached the front door and looked down at himself. He’d snuck out of the house wearing a t-shirt and a set of jeans and then gotten changed at the party. He was currently sporting a cute goth look with eyeliner, a mesh top, ripped leggings and black boots. He’d intended to change back before he got home, he didn’t need his Mom’s prissy, condescending critique of his fashion choices. He was home now, though, and he realized that he must have forgotten his street clothes in his friend’s car. He paused for a moment, wondering if he should stop and go searching for them, or if he should just risk his Mom seeing him in this outfit.

Casper gently placed his hand on the doorknob and twisted it, opening the door as silently as he could. There was a light on, but his Mom had probably just left it on for him, she wasn’t necessarily waiting to ambush—

She was there, sitting in a living room chair like a gargoyle with her hands folded in her lap. “Do you have any idea what time it is?”

“Tsh.. later than… should be.” he slurred, still rather tipsy.

“And… what the fuck are you  _ wearing?  _ Why are you  _ crossdressing?? _ ” Her voice went up an octave and her hands balled into fists.

“I’m not! This is just… It’s...! You wouldn’t understand.” he tried to explain to her, but she was too angry and he was too tipsy.

“I understand perfectly. You’re a goddamn pervert, just… Just like  _ Her! _ ” Even as she said it, the two of them froze, the weight of her words squeezing them both.

“Like who, Mom?” Casper asked softly.

“You  _ know. _ ” His Mom, Cassandra, replied with ice in her voice.

“Yeah, I do. You won't ever talk to me about her but I know,” Casper muttered bitterly. She’d meant Evelynn, his other Mother. The two had split up when he was young, and Cassandra refused to talk about her save for small outbursts like this.

Casper slammed the door to his room, exhausted, frustrated, and still pretty drunk. The two of them had fought for over an hour, and he was tired. Not just tired tonight, but tired of fighting with her in general. She’d always been difficult, but the second he’d started expressing an interest in being anything other than a musclebound macho guy, she’s started really escalating on him. He’d wanted to drop out of hockey to make more time for theatre and choir, and she’d lost her mind. One of his friends had come out to him as trans, and she’d mysteriously found a new job across the city that made it almost impossible to see him anymore. He’d come to terms with his bisexuality a little while ago, and he was absolutely dreading that conversation with her, if it ever came to it. She’d said… he was just like her, like Evelynn. His Mom’s definition of a pervert was definitely one that she played fast and loose. Maybe Evelynn was just… cool? Maybe she’d be accepting? Cassandra had seemingly sworn off any sort of homosexuality, even though she hadn’t said it, but maybe Evelynn hadn’t?

The thought stuck in his head so poignantly that he remembered it in the morning when he woke up. He went to his computer, and started to search. He combed through court records until he found Cassandra’s name change. She’d changed her surname from Davis-Wu back to just ‘Wu’ seventeen years ago when he’d been two. He then jumped onto social media, searching for Evelynn Davis and… just like that, he found her, his other Mother. She lived in Vancouver. There was a border between them, but geographically, she was closer to him than any other major city. It was only a few hours by bus. He opened up a Direct Message, typed ‘Hi, I think I’m your Son, Casper?’ into it, and stared at the screen, frozen. He squeezed his eyes shut, looked away, and hit enter on his keyboard, sending the message. He stared at the screen, at the sent message for a little while, feeling some anxiety bubbling up. This was stupid, he shouldn’t have—

Casper Wu (09:42 AM): Hi, I think I’m your Son, Casper?   
  
Evelynn Davis (09:45 AM): Oh my Gods, Yes!!! Does Cassandra know you’re messaging me?

Casper Wu (9:48 AM): No. I’ve been having a lot of problems with her lately…

Evelynn Davis (9:55 AM): Oh Honey, you’re preaching to the choir on that one. Honestly, I’ve wanted to reach out and talk to you for years but there’s already enough bad blood between Cassandra and me, and I didn’t even know if you’d want to hear from me.

Casper Wu (10:01 AM): She never talks about you. We had a fight and she called me a pervert ‘just like you’ last night and I dunno I’m getting so sick of fighting with her. Seemed like a good excuse to see if I could find you.

Evelynn Davis (10:10 AM): Tell you what, I’m going to extend an open invitation to you to come stay with me. (Temporary or long-term) You’re 19 now, you can make your own decisions.

Casper Wu (10:12 AM): Live with you? IDK that seems like the nuclear option, doesn’t it?

Evelynn Davis (10:14 AM): LOL! I just meant for a week or so, silly. Maybe if Cassandra realizes that you have some agency of your own, it’ll make her cool down a bit.

Evelynn Davis (10:16 AM): Honey, I’ve got to go to work now. I’d love to keep in touch even if you don’t ever find your way out here to see me. Best of luck with Cassie <3

Casper Wu (10:16 AM): Thanks. I’ll think about it.

***

A week later, Casper stepped off the greyhound carrying his suitcase, looking around the bus terminal for a woman he’d never met. He spotted her fairly quickly, she was a tall woman, easily towering over Casper or Cassandra who were both only about five foot five even without the two-inch heels she was currently wearing. She had thick, dark hair that would have been down to her shoulders but it was currently done up in a ponytail and paired with long, side swept bangs. She wore a simple white dress with a V that revealed a decent amount of the flesh on her prominent breasts. She had dark green nail polish on and was carrying a cute handbag. She spotted him too, and waved energetically, walking over to him with a spring in her step.

**_  
_ ** “Casperrrr!” Evelynn squealed, happily. She grabbed him in a crushing hug and energetically lifted him clear off the ground. His face got buried in her cleavage and he blushed profusely as he tried to squirm free of her grasp. Evelynn proved to not only be quite a bit taller than him but quite strong too, and she squeezed him breathless with the hug.

“Gosh, I wasn’t sure that I’d ever see you again, you got  _ so  _ cute on me!” Evelynn planted him back down on his feet and leaned down to plant several kisses on his forehead, cheeks, and lips. It was bizarre to him to have her being so affectionate with him, his other Mother had always been so stoic. Getting even the most brief, chaste hugs out of Cassandra had been a chore.

“H-Hey,” he mumbled, smiling a little, her affection and enthusiasm proving to be infectious. Evelynn squealed happily and smiled at him with her hands on his shoulders. “It’s like a dream. You’re… wow! You must be so tired from the bus ride, come on I’ll take you to my place.” She quickly snatched Casper’s bag from him before he could protest and led him out into the parking lot, humming happily to herself as she went. She had a spring in her step and a bubbly energy about her that Casper couldn’t take his eyes off of. The contrast between Evelynn and Cassandra felt like something that belonged in a theatre performance, and it boggled his mind that the two women could ever have been a couple at all, let alone one that had had him.

Eve took him to what he thought looked like a very nice car (Not that he knew anything about cars, really.) He did know enough to recognize that it was much newer than anything Cassandra had ever owned. She threw his bag into the trunk and moved quickly, opening the door for him. He couldn’t help but giggle at her enthusiasm, and got in.

“So how was the trip?” she asked, settling in next to him in the driver’s seat and starting the car up.

“Bit long, but it was alright. They searched me for drugs at the border, the racist pricks.”   
  
“Yeah, no kidding,” Evelynn sighed and shook her head. “Did you end up telling Cassandra you were coming?” she asked. Her voice had a bit of an exploratory probing to it, like the words were caustic and dangerous to handle.

“No. I tried to, but, she’s just… She’s so hard to talk to, and it only gets harder. I ended up packing a bag and my passport while she was at work, using the ticket you sent me and just… coming.” He laughed nervously, hoping Evelynn wouldn’t be mad that he’d snuck away from Cassandra like this.

Evelynn put a hand on his shoulder. She was still driving so the glance she shot him was passing, but somehow it had a lot of weight to it. “Something happen recently?”

“I came home, and I was wearing… I wasn’t even  _ really _ crossdressing. I went to a party, I had on a fishnet top and…” he trailed off. They were at a stoplight, and Evelynn was staring at him, wide eyed like a puppy.

“I bet you’re ADORABLE.” she gushed. “The girls must be all over you!” 

Casper cleared his throat, squirming uncomfortably. He felt like he was reasonably popular with girls, but not… _just_ with girls.

Evelyn glanced at him out of the corner of her eyes. “Not the girls?” she asked carefully, as if feeling out the sentence.

“I mean” he said, feeling a knot of unease deep in the pit of his stomach, “maybe not  _ just _ the girls?” Even as he said it, he could hardly believe it. He’d been struggling to hide this from Cassandra for almost a year and now he’d blurted it out in five minutes with Evelynn.   
  
He flinched at Evelynn’s squeal of delight. “Oh I bet you break so many hearts. You clearly take after me!” There was a note of pride in her voice at the claim.

“You aren’t upset?” he asked, taken aback by the strength of her approval.

Evelynn laughed. “Oh please! Honey, it’s 20XX. Only boomers are straight anymore. I married your mother, do you really think I’d be upset that my son is bi?

Casper thought he heard a faint note of bitterness at the mention of his mother. He had sometimes thought it was strange that Cassandra had been married to a woman and then pivoted so strongly in such a prudish direction. If anything, it made sense that Evelynn wouldn’t have done exactly the same. She might be able to relate to him more than Cassandra else possibly could. “I haven’t really told Mom, I don’t think she’d take it well.”

“Really?? I knew Cassandra had turned into a stick in the mud but to think that  _ our _ son would be afraid to come out to her? Well, it’s settled! I’m going to show you I’m the cool Mom. We are going shopping for you this week. Anything you want.”

“Evelynn, you don’t—”

“For one thing, young man, I am your Mother, call me Mom. For another, I  _ want _ to take you shopping and there’s nothing you can do to stop me.”

“I… I can’t. Cassandra is Mom. You’re…” He paused.

“That’s fine. I can be Momma. Mother? Mam? Ma? Mommy?” She shot him another look, smirked, and nodded. “Yep, that’s the one. Mommy.”

Casper laughed. “No, that’s…”   
  
“Settled? Darn right it’s settled,” she laughed back at him, and completely shut down his attempts to argue the point. He didn’t actually  _ call  _ her Mommy, rather he just avoided calling her anything at all as best he could. Her house was out in the suburbs, and it took them about an hour of driving to get there. They mostly chatted about him, his interests, his life. He’d seen from her profile on social media that she was an author, but not gotten much else out of it. Her actual house was… surprising to him. He’d thought Vancouver was a big, urban area, but somehow she managed to drive him to a relatively rural road without leaving the city. It was dense with trees, like a conservation area, and she drove him up a winding road to reach her house. It wasn’t the only house in the area, but it was pretty quiet and secluded just the same.

“No place like home, eh?” Evelynn asked. “I’ve got a room you can stay in. You wanna order a pizza for tonight?”

“Sure,” he agreed, looking around the house. It wasn’t a mansion, but it was probably four times the size of the little house that he lived in with Cassandra in Portland. Evelynn gave him directions to the room, and he carried his bag there. He clicked on the light, and paused in the doorway for a moment. The room before him was the pinkest, frilliest, most stuffed-animal filled room he’d ever seen. It looked like something out of a movie.

He chuckled a little, it was actually kind of refreshing. Cassandra had freaked out over him expressing himself in even the least non-traditional way, and here Evelynn was giving him a pink bed to sleep in. The room had several dressers, a big closet, and a nice desk with a computer on it. He dumped his bag on the bed and wandered back off to find Evelynn.

“What’s with the room Mo—” He paused as he entered the living room/Kitchen and saw Evelynn with her phone in hand. She looked at him, and grinned.

“Say it, or the pizza doesn’t get ordered,” she said with a low, teasing, almost flirty voice and a playful smirk. The two of them stared at one another for a few seconds, Evelynn’s eyebrow slowly arching higher and higher.

“Mommy, what’s the story with that room?” he relented, laughing a little at his Mommy’s absurdity.

“Oh, I had an exchange student in there last year. I kind of spoiled her, she was such a darling. It’s not a problem, is it? I never got around to donating away her things.” She dialled, and raised a finger to stymie his response as she spoke to the pizza place.

“No, it’s fine, it’s just for the week. I’ll just move the stuffed animals around. Can I use that computer, though?” he asked once she was done ordering.

“Oh, of course you can. It should be able to connect to my Wi-fi but the password is on the router if not.” She settled down on the couch and patted the cushion next to her. He came over and settled in next to her. She crept a little closer to her and put her arm around his shoulders. “Gosh. You look so much like her, you know? People ever tell you that?”

“Dunno… Mom doesn’t really… get out much, anymore. Can I ask… What happened between the two of you?” Evelynn’s arm engulfed him and he found himself being drawn into her. His head pressed into the side of her left breast and he tried not to pay too much attention to it.

“Do you know what I do, baby?” she asked.

“Umm, you’re an author?” he replied.

“Yup. A lot of what I write is  _ very  _ naughty, though. A little while after you were born, Cassie just sort of… assumed that I’d stop? She came across my latest manuscript and sort of… went off on me. Started screaming about setting a wholesome example for you. Honestly, I was totally blindsided by it all, I had no intention of changing what I was writing, and I never thought we’d raise you as some sheltered kid who didn’t know what sex was. The fighting got really bad and she just… took you and left. Went back to America.”

“She… she was allowed to do that?” Casper asked, a little stunned. He’d expected some bad blood between his two parents, but something like this was kind of shocking.

Evelynn sighed, sounding genuinely sorrowful for the first time. “I didn’t have any excess capital to commit to a lawyer at the time, and, honestly, I expected Cassandra to play fair. She didn’t. Cassandra’s brother took the case and totally blindsided me. They found a sympathetic judge that totally ate up their argument about my writing being inappropriate. She got full custody almost before I realized what was happening.” She looked away from Casper, a pained expression on her face.

They were quiet for a few moments, and then Casper leaned in and gave her a hug. The conversation diverted from there and he went on about the things he was doing, the choir he’d stealthily joined, the school he was applying to, things like that. The pizza took a while to arrive, and when it did, the two of them settled down on the couch to watch a movie on Evelynn’s rather large television. Before he even knew what was happening, he melted into Evelynn’s softness and warmth and drifted into a doze.

He dreamed that he was kissing someone. He wasn’t sure who, it was more of a vague sense of another person. They felt so nice, so warm, and it was so amazing to be kissing them. He moaned softly, gyrating his hips, a mysterious friction against his cock making sparks run through his body. His tummy contracted, twitching, and he whimpered as his hips bucked. He felt sooooo good, and a warmth spread throughout his body starting at his crotch. He gasped, and as he noticed something oppressive and wrong on his face. He felt a tiny surge of panic as his breath didn’t quite come as it should.

He gasped, twitching in panic, surging awake. His face was pressed firmly into Evelynn’s armpit and he’d gotten a mouthful of her dress as he’d tried to breathe in. There was a bit of a lingering taste of sweat and Evelynn laughed at him as he sputtered a bit.

“Oops?” she asked. “Twisted wrong in your sleep, huh?” She raised her hand to her mouth and licked the webbing between her thumb and forefinger.

“Y-Yeah,” he murmured, wiping a bit of the drool off his face. He noticed a moment later, that his cock felt wet, and in horror, he looked down to see the big wet stain in his pants. The dirty dream had made him cum in his pants right next to Evelynn. He had a moment of terrified embarrassment as he squeezed his thighs together, positive that Evelynn had noticed and was going to be furious with him for being such a pervert.

“I think it’s time for you to get some proper sleep, young man. I won’t be around much tomorrow but you can have the run of the house. I’ll have more time for you after that, okay?” Casper blinked in confusion as Evelynn spoke. Had she… not noticed? She musn’t have. There was no way Evelynn was nice enough to just pretend she hadn’t noticed, she’d teased him about everything else.

“Yeah. Thanks, E— Err, Mommy.” Evelynn beamed happily as he called her Mommy and kissed him on the top of the head. He squirmed a little, hoping to get his back turned to her as soon as possible to conceal the wet spot. As quickly as he could, he bid her goodnight and got swept up in another energetic goodnight kiss before he returned to his new room. As he crawled under the fluffy bedsheets, relief flooded him that he hadn’t made a complete fool of himself, and he drifted off to sleep feeling strangely accepted for the first time in a long while. 

***

The next morning, after getting dressed, Casper booted the computer up, and sat back waiting for it to load. It snapped to life fairly quickly, dumping him onto the desktop. He was a little surprised, he’d been expecting some old dinosaur of a computer for the spare room, but it actually seemed like it ran better than what he had at home. He opened up the web browser to watch some videos for a little, and instinctively hit the shortcut to bring up browser history so that he could pick up where he’d left off. Of course, it wasn’t there, and he chuckled to himself as he realized his error, going to close the tab. And then… he saw the browsing history.

<Crossdressing slut gaped open by BBC>

<Sissy bitch used and abused>

<HYPNO: Be a good cock whore for Mommy>   
<T-Girl spitroasted by huge strapon DICKS>

<Broken In(FutaxFemboy)>

<Training the Sissy Maid>

<Dark Horse>   
<femboy cums hands-free in chastity - what a good girl!>

<Sissy Mind-Break>

<FISTING! Force-Femmed twink takes it wrist-deep>

<Locked in Chastity forever - Eternal Servitude Pt.3>

He knew it was porn at the first glance, that much was obvious. It just took him a few seconds to realize the common theme. He stared at the… extensive list for a few seconds, somewhat overcome with morbid curiosity and somewhat overcome with just regular curiosity. He wondered if it was the exchange student’s porn history, or if it was Evelynn’s. He ended up closing the web browser, getting away from the computer and wandering through the house to think a little.

Evelynn’s house was nice, well-decorated, tasteful. He felt a little out of place, almost like he wasn’t supposed to be touching anything. As he passed through the living room, he spotted something he hadn’t seen the night before. There was a door in the middle of the hallway, one that looked like it might lead to a basement or something. It was locked, but not just locked, it had a ridiculous padlock on it. He approached the door curiously and inspected it for a moment. It wasn’t a normal-looking padlock, even. It actually looked custom-made, with a big, fancy keyhole and huge, heavy locking mechanism. It was like something that you’d expect to see on a movie set attached to a chest full of cursed pirate gold. He gave it a bit of an experimental tug and pulled on the door to see if it was just for show, but the door didn’t even begin to budge and clearly  _ was  _ very locked.

“Guess I’ll have to ask her about it,” he mused, and went looking for some food. He found some cereal easily enough and went through cupboards until he found bowls, and then drawers until he found a spoon. His phone buzzed as he ate, and he peeked at it to see that Evelynn had texted him.

Evelynn Davis (8:16 AM): Morning, sleepyhead! Let me know if you can’t find anything around the house. I won’t be back until late, but I promise I’ll make time for you tomorrow. See you tonight <3

Casper puttered around the house for a little. He went back to the computer full of sissy and trans girl porn and avoided it, watching some silly internet videos instead. Afterwards, he explored the house a little more and ended up opening one of the upstairs doors. It was Evelynn’s room, clearly. He immediately felt like he was intruding. He stopped, and intended to turn around and leave, but then, something caught his eye, and he did a double take. There was a flesh-coloured cylindrical object, discarded at the foot of the bed. His morbid curiosity overwhelmed him, and he stepped forward to confirm.

It  _ was  _ a fleshlight, a used one. A tiny stream of what could be cum or lube had oozed out of it, and when he stepped forward, he smelled it. Definitely cum. He shook his head and backed away, leaving Evelynn’s room and closing the door behind him. He shouldn’t have done that, shouldn’t have snooped. He couldn’t help but wonder what that was, though. Had Evelynn had a guy over, that night? If so, why would he have used a fleshlight? Why would it have been left at the foot of her bed, discarded as if in haste and afterglow.

He ended up going for a hike, making his way through the trees and hills surrounding Evelynn’s house. He found that there were only a few houses in the immediate area, but when he climbed a tree, he was able to get a good enough view to see that the rest of the city wasn’t far off, he was still surrounded by civilization. It was maybe a twenty minute walk to the nearest major street. Satisfied, he climbed down and headed back to Evelynn’s house, and started taking a few notes of places he wanted to go in the city while he was there. An idea occurred to him and he grabbed his phone to text Evelynn.

Casper Wu (4:45 PM): Mommy, do you mind if I make dinner? Can I use what’s in the fridge and pantry?

Evelynn Davis (4:51 PM): Oh my Gosh! I get a home cooked meal?? Use whatever you want Sweetie. Wow, I’m excited, you’re so sweet!!! <3 <3 <3

She sent him a barrage of emoji with that last message, more than she normally used. Casper wasn’t entirely certain what she was trying to communicate with them, but it was definitely positive, so, with that settled, he went to the kitchen. He found enough ingredients to make curry, and so he started cooking. He was getting close to being finished when the door opened, and Evelynn entered, singing energetically to herself. 

“Darling~” Evelynn crooned, sweeping into the kitchen and wrapping Casper up in another smothering hug as he worked. “This looks delicious, my adorable little housewife. How was your day? Keep yourself occupied?” she asked.

“It was fine, I went for a walk. What’s that giant lock on the basement door?”

“Hah! It was a gift from my publisher, actually. Bit of an inside joke from one of my books. The basement’s not safe right now so I figured I may as well use the silly decorative padlock. It’s cute, isn’t it? I think it looks very mysterious and foreboding.” Evelynn giggled at him and poked him in the ribs with a mischievous grin.

“So, no bodies stashed down there?” Casper snickered.

“Nah, just whips, chains, and restraints.” Her grin grew, challenging him, daring him to call her on the bluff, but he didn’t. She put some of her things away, still humming to herself. He served the curry, which had turned out quite nicely, and Evelynn seemed to barely be able to contain her eagerness as he did. As he sat at the table, Evelynn mischievously placed a pair of wine glasses onto the table next to the plates, and grinned at him, brandishing a bottle with an eyebrow raised in question.

“Oh, sure? It’s alright? I’m not twenty one.” he said with a soft laugh.

“Legal drinking age is nineteen up here, darling~” she giggled at him, pouring the wine with a wink. The two of them chatted and ate for a little while, Casper feeling a bit of a warm buzz from the wine and inexplicably, a weird half-chub that he did his best to ignore. Evelynn _ was  _ very beautiful and nice, and the boner… no it wasn’t about her. It had to be just hormones or something.

“So, Sweetie. I was thinking today.” Evelynn changed the subject abruptly away from science fiction. “I assume nobody ever had the backdoor chat about safe sex with you, huh?”

“Well, Mom avoided it like the plague but I got the basics from school and the internet. Condoms, pregnancy, all that stuff.” He answered. It was honestly kind of cute that she was worried about him like that.

“Oh, darling, no. I meant…” she made a circle with her thumb and pointer finger on one hand and then moved her other pointer finger through them back and forth a few times.

“Umm…?” he frowned, confused. “I don’t follow.”

Evelynn snickered and leaned in. “Backdoor. Butt stuff.  _ Anal Sex. _ ” she spoke the last one slowly and loudly, pausing after every syllable. She then put four fingers together to continue her gesture. The digits no longer cleanly fit into the circle formed by her fingers and her teasing grin grew wider. Her lewd gesture slowly became significantly more lewd as she continued trying to roughly force them further inside.

“Okay, Okay!” Casper both snickered and blushed. “What about Butt sex?”   
  
“I can’t have my son getting hurt when things get put into his cute little tushie!” Evelynn gave him a serious look, folding her hands on the table.

“Hey… maybe I’m the one who puts… uhh, things. Into other people’s—”

Evelynn burst out laughing. Casper scowled at her and crossed his arms. “What’s so funny?”

“Oh come on, sweetie, I can smell a bottom a mile away. Don’t be shy, the world needs bottoms! Gosh, there’d be an awful lot of cold dicks otherwise.” Casper’s embarrassment finally got the better of him and he looked away. As he broke eye contact, Evelynn cackled victoriously. “Knew it!”

“Mommy, c’mon, this is embarrassing.” Casper muttered.

“Alright, alright. I’ll just talk to myself and remind myself how important lube is, how spit isn’t lube, and about how you always need some warm-up because one of your sphincters is involuntary.” Casper burned with awkward embarassment as Evelynn cited off a bunch of rather detailed but very sterile information about anal sex. His ears did perk up a few times at bits of information he hadn’t known, or that he’d thought were myths. He avoided giving her the satisfaction of confirming that he needed to hear it, though. He thought about it a little and it was pretty funny actually that Evelynn was a huge over-sharer and Cassandra was so stoic. As their meal wound down, Casper’s phone rang, and he glanced over to see something he’d both expected, and that made his stomach twist into a knot. Cassandra was calling him.

“I… should take this,” he murmured, looking away from Evelynn and accepting the call.

“Uhh, Hey,” he answered.

“Really? You vanish, don’t even leave me a note, and all I get is a ‘Hey’?” Cassandra wasn’t shouting but her voice was full of malice.

“Yeah, well whose fault is it that we’re not on speaking terms right now?” Casper replied, scowling. Evelynn set her fork down and looked at him thoughtfully. She mouthed the name ‘Cassandra’ to him, eyebrows raised questioningly, and he nodded.

“Don’t you Dare! I cannot believe this. Where are you?” She snapped, her facade of control starting to slip away.

“I’ll be home early next week. I’m fine, you don’t have to worry.”

“That’s not what I asked you.”

“It’s just… I’m staying with Evelynn for a few days. It’s no big deal.” Casper felt a tremor run through his body. He didn’t want to have this conversation. Why’d he even answer the phone?

“Very funny. Where are you?”

“Vancouver. I’m just getting to know my other parent. Is that so bad? Don’t I have that right?” he shot back, getting riled up by the third degree coming from Cassandra. It was in that moment that he realized he was a little tipsy again. Evelynn had been generous in refilling his glass and he wasn’t used to drinking wine.

“Wait… Casper, you’re joking, right? Please tell me you’re not with her right now.” Cassandra’s voice changed ever so slightly. She sounded… afraid?

“Yeah, she’s right here, we just had dinner.”

“Oh my Gods, Casper, no. no, no, no, no, no, you can’t. You need to get out of there you need to get away from—”

“Oh come on, Mom, this is just sad. I’m an adult now, you can’t keep me locked away in my room.” Casper growled in annoyance. He knew that Cassandra didn't like Evelynn, but to put on this act to convince him that she was dangerous was pathetic.

“CASPER, PLEASE, LISTEN TO ME.” Her voice was panicked, desperate.

“No! Shut the fuck up, for once! It’s just a week, Mom, I’ll see you on tuesday.”

“CASPE—” he hung up, getting the speaker away from his ear with a wince.

“Sounds like that went well,” Evelynn murmured softly. Casper barely heard what she said. He was trembling. He was so tired of this. So tired. He couldn’t even have dinner with Evelynn without Cassandra… doing this.

“I’m gonna go to bed,” he whispered, picking his phone up.

“Hey, sweetie, why don’t we talk about this?”

“Tomorrow… tomorrow.” he stood up from the table abruptly and rushed away to his room. Evelynn called after him again but he ignored her,moving through the halls to his room as quickly as a walk could take him. He flopped down on the bed, feeling the tears well up. He couldn’t keep doing this with Cassandra. It was getting harder and harder. He choked back a sob, and shook his head. He was also still super horny and it seemed to be getting more and more intense, like his body was out of control. His boner hadn’t gone down and in fact it was starting to throb needily, demanding his attention.

“What the fuck is wrong with me?” he growled softly, twisting and turning. He buried his face in his pillow, trying to think unsexy thoughts, trying to… ugh. He jumped out of bed, kicking his clothes off and digging out his pajamas. His cock pulsed and twitched demandingly as he freed it from the jeans, but he ignored it. He wasn’t in the mood, he just wanted to forget about Cassandra for once. He crawled under the covers, his anger at Cassandra slowly but surely being replaced for his anger at his stupid libido that wouldn’t leave him alone.

“Fine!” he muttered, reaching down and grabbing it to start stroking. He masturbated out of spite and out of a desire to be able to get some sleep, but he gasped and squealed as the shock of pleasure caught him off-guard. It felt so nice, so intense, it was an outlet for an intense amount of lust and horniness that he hadn’t realized he was harboring. He tried not to think about why he was so horny, choosing to blame his hormones, and instead just stroking rapidly, moaning and whimpering softly.

Suddenly, the door squeaked open, Casper yelped in surprise as he realized Evelynn had walked in. He immediately stopped what he was doing and squeezed his thighs together, as if to suppress his lust. He looked over his shoulder wide-eyed, burning with embarrassment that he’d been caught.

“I know it’s hard, sweetie, but Mommy’s here, you don’t have to cry by yourself,” she whispered, crawling on top of the bed next to him and putting her arm around his chest, hugging him close to her. It didn’t seem like she’d realized that he’d been masturbating. Casper realized that she probably heard him whimpering and moaning and mistakenly thought he’d been crying. Part of him wanted to correct her, but, well...

“M-Mommy, it’s… uhh...” Casper murmured incoherently, trembling with embarrassment and residual lust. His cock still throbbed needily, desperate for the release he’d promised it. 

“Shhh, it’s okay baby,” Evelynn cooed into his ear, hugging him tight, her fingers running through his hair. “You don’t have to explain anything to me. I’ve dealt with her before, I know how hard it is.”

Casper squirmed uncomfortably. He had a boner trapped between his thighs that wasn’t going away, and Evelynn was so soft, her big tits were pressing heavily into his back. Her warm breath tickled his ear and he whined softly in frustration.

“What’s the matter, baby? You’re so tense. Mommy’s here, you can relax.” she whispered. Her other hand rubbed his chest gently. It drifted down until it was on his stomach, and she squeezed him closely, pressing his body against hers.

“I-It’s nothing, I was…” Casper murmured lamely. He didn’t know what to say. Just going to sleep? Crying over Cassandra?  _ Jerking off? _

Evelynn’s hand dipped a little lower, touching first his thigh, and then, ever so gently, her fingers brushed up against the hard, throbbing tip of his cock. Casper jerked as if he’d been shocked, pulling away from her a little bit. He was being firmly squeezed and cuddled by Evelynn though, and she was stronger than she looked. His attempt to squirm away barely got him any space at all.

“Oooh,” Evelynn laughed softly in his ear. And then, slowly, her hand dipped under the waistband of his pajamas, her fingers delicately yet firmly wrapping around his cock. Casper gasped. In shock? In denial? Pleasure? He wasn’t sure. “I see what you were doing,” Evelynn teased gently, her hand giving a painfully slow, teasing squeeze and stroke.

“M-Mommy, don’t…” Casper whined, but even as he did, his hips twitched, thrusting gently into her hand. He was so horny he couldn’t think straight.

“Don’t worry, baby, it’s just us here. Mommy will make you feel better, okay?” As Evelynn spoke, she moved her other hand from petting his hair to his neck. She slowly, sensually wrapped her hand around his throat, not choking him or constricting his airways at all, but she simply held him there possessively as her other hand started to stroke him. She swung a leg up and over his hip, pinning him to the bed and to her and she started to pump his cock. Casper moaned out loud, unable to protest or struggle, so overwhelmed in his feelings of ecstasy as Evelynn slowly, deliberately jerked him off.

“Doesn’t that feel nice? Nothing complicated. No worries, just Mommy’s nice soft hand for you to cum in. Don’t be afraid, sweetie, moan all you want, let Mommy know if she’s doing a good job.” Evelynn’s husky voice was right in his ear, her breathing intense. Casper did as he was told, moaning, writhing ineffectively in Evelynn’s embrace. Erratically twitching and humping his hips into the soft, squeezing warmth of her hand. Her motions were slow, deliberate, and steady. Casper felt like he was going insane, he started spasming and thrusting against Evelynn’s, desperate to increase the stimulation, desperate to cum.

“M-Mommmmyyyy~” Casper whined, any other words too complicated for him to form.

“Hmm? Does Mommy’s sweet little girl want to squirt her sissy cum?” Evelynn teased, the hand around his neck squeezing gently, silently communicating the control and the power she had over him in that moment.

“Y-Yesssss,” Casper screamed, the strangeness of Evelynn’s comment not even registering in his brain before the storm of passion that was overwhelming him. Evelynn stopped stroking for a moment, squeezing his cock with all her strength, the vice grip making him gasp in something between pleasure and pain. Then, she started to stroke him more quickly, and Casper squealed, arching his back as his pent up lust was quickly built up past the breaking point.

“Mommy! F-Fuck!” Casper babbled. He twisted his head to the side a little, squeezing his eyes shut as the orgasm quickly built up. Evelynn’s lips met his, and her tongue slipped into his mouth as he came. Casper moaned into the kiss, passively letting Evelynn kiss him and her tongue gently explore his lips. He came with explosive intensity into Evelynn’s steadily stroking hand, and she immediately twisted her grip a little, still squeezing and stroking but keeping her hand cupped over the tip of his cock. His body slowly went limp, drained of strength as he rode out his orgasm, Evelynn still holding him close, trapping him, kissing him as slowly and deliberately as she wanted to. She moaned softly, thrusting her tongue into his mouth, dominating him with her soft lips. After a while, she finally broke the kiss, purring happily in his ear.

“Gooood girl,” she whispered, squeezing out the last drops of his cum from his exhausted body. Casper breathed a sigh of relief as she removed her hand from his overly-sensitive cock. A moment later, she slipped one of his fingers into his partially-open mouth, and he immediately tasted the slightly sweet, bitter taste of cum. His cum.

“Clean up after yourself, baby. Don’t make a mess on Mommy’s sheets,” she cooed softly, slipping a second finger into Casper’s mouth. Part of him thought he should resist, but he did this with his own cum sometimes anyway, and soon a third finger joined the first two. He sucked on them gently, and Evelynn immediately purred in approval, whispering encouragement into his ear as she slowly pistoned her fingers in and out of his mouth. With her fingers clean, Evelynn slowly withdrew them and kissed him on the cheek, relaxing her pinning grasp on him just a little bit.

“What a good girl~” Evelynn murmured, one of her hands wandering down to cup his butt and give it a tiny squeeze. “You get some sleep now, okay? You’ll feel better in the morning.” She kissed him again on the top of his head and delicately slipped out of the bed, letting him drift off to sleep almost immediately.

***

Casper awoke the next day with the first rays of morning sunshine coming through the window. The smell of bacon was filtering into the room and he rubbed his eyes, confusing and conflicting thoughts running through his head. What happened last night? He’d fought with Cassandra over the phone again, but then…? Had he and Evelynn…?

No, that couldn’t be right. He did vaguely recall Evelynn jerking him off, but he’d been a little drunk and inexplicably horny. It had to have been some bizarre oedipus complex dream. He wandered into the kitchen to see that Evelynn was wearing nothing other than a bra, panties, and an apron. She was frying bacon in one pan and working on an omelette in another.

“Good morning~” she trilled, taking a moment to plate the eggs and bacon and set them on the table for him. “You sleep okay?”

“Uhh, yeah,” Casper murmured, taking a seat and avoiding staring at Evelynn’s scantily-clad body. “Mommy, did… did something happen last night?”

“Well you got a call from Cassie, we snuggled a bit, and then you fell asleep. I think I may have refilled your wine a bit too generously,” she laughed, turning the heat down and plating her own breakfast.

Casper shook his head a little. Evelynn stroking his cock, Evelynn’s fingers in his mouth, he couldn’t tell if it was real or not. “Ah… nevermind. Mom always gets to me, I guess.”

“Yeah, she does that. Believe me, baby, I know,” Evelynn sat down across from him and slapped a sheet of paper down onto the table between the two of them.

“What’s this?” he asked, taking a bite of his omelette as he glanced at the paper. The eggs were… alright. Evelynn was clearly not much of a cook, she’d overcooked the eggs a bit and hadn't used enough pepper. Still, it was more than Cassandra ever really did for him. The paper looked like a list of names? Maybe a list of stores?”

“I told you, silly, I’m taking you shopping. Those are just some ideas of places we could go. There’s no way a healthy young man like you doesn’t need  _ something _ . Even if you don’t want some cute clothes from Hot Topic or some skirts and panties, we can get you some more practical things, you look like you need some new shoes, for instance.”

“M-Mommy! I do not need… why… I told Mom, I’m not crossdressing, it’s just…” Casper blushed and sputtered.

“Methinks the lady doth protest too much,” Evelynn snickered at him with a grin. “But really I was just letting you know that nothing is off the table. I owe you seventeen birthdays of presents and I can certainly afford to spoil you a little, honey.”

“Is… is this a sex shop?” Casper asked, pointing at one of the stores on the list.

“Yeah, but they have some cute latex clothes, too. You haven’t  _ really  _ worn tight pants until you’ve squeezed your way into a pair of rubber pants coated in silicone lube.”

“I…” Casper trailed off. That actually sounded awesome. “Alright, we can look.”

In spite of his earlier reluctance, Casper soon found himself swept up in Evelynn’s eagerness, and was eagerly participating in the shopping trip. He picked out several cute tops and pairs of pants, a bunch of really nice eyeliner that was far superior to the stuff he’d been stealing from the bottom of Cassandra’s makeup cabinet or buying on sale at drugstores. She took him to a ramen restaurant for lunch, which he was quite skeptical about since his mental image of ramen was instant noodles. It ended up being the best noodles he’d ever had and he made a mental note to scour portland for similar restaurants when he got home. It was late afternoon by the time they drove up to the sex shop and parked off to the side. 

“So, ummm…” Casper murmured, wondering if he actually had the courage to go into the shop with his mother.

“Yeah?” she asked, shutting the car off and unbuckling her seatbelt.

“We’re going in… together?” he asked.

“Yeah, is that a problem? I can keep the fact that I’m your Mommy on the down-low, if you’d like. If I grab your ass in the shop they’ll probably just think I’m a cougar and you’re my boy-toy.” she winked at him.

“I don’t think that’s necessary,” he laughed, shaking his head and getting out of the car.

“Alright, open offer though.”

“Do you want to grab my ass, or something, Mommy?” he asked. For good nature, he bent at the waist a little bit and wagged it slowly in her direction. He figured if it was fair that she flustered and embarrassed him, he could do the same to her.

“Does a woman dying of thirst want a drink of water? You have the sweetest, fattest, most slappable ass I’ve seen all year, baby. I could just bend you over the hood of my car right now and make you squeal like a—”

“Alright, alright,” Casper burst out laughing, realizing that embarrassing Evelynn was probably the most futile endeavor in the universe. When he looked at Evelynn, she has an extremely serious expression on her face. And he chuckled again.

“Let’s just go,” he relented. They went into the store together and by the looks of it, it was divided into two halves. One had shelves and displays full of dildos and various sex toys, the other was mostly clothes and various fetishwear. Casper went ahead of Evelynn towards the section of the store full of clothes. He took one step, and then  **_Wham._ ** Evelynn slapped his ass so hard that her fingers dug into the flesh of his asscheek. Casper yelped in distress, blushing furiously, but just as soon as she’d started, she let him go and walked past him into the clothing section.

Casper looked around the store for a second, and saw one of the cashiers, a pretty girl in her twenties smile and wink at him, but otherwise nobody seemed to notice. “Just for that you’re buying me two pairs of pants,” Casper murmured to her when he caught up with her.

“Fair enough, fair enough,” she snickered.

Casper focused on the pants for now, quickly finding several that he liked. One of the store attendants came over and helped him try them on with the assistance of copious amounts of baby powder. He squeezed his way into one of the pants, and moved around in them a little to get a feel for it. As he ran his hands along the shiny, clingy material that was hugging his body, he had a bit of an epiphany. He knew people were ‘into’ rubber and latex, but he hadn’t really understood it until just now. The way it clung to him like a second skin, the feel of it, the sound it made when he moved. He knew that Evelynn had successfully opened a bit of a pandora’s box for him.

“Show us! Show us!” Evelynn’s chanting voice came from outside the room. Casper opened the door and came out of the changing room. Evelynn gasped as she saw him, putting her hands over her mouth. Casper did a little twirl for the two of them, and Evelynn squeaked.

“Looks like a good fit,” the store attendant commented, nodding in approval.

“I can die a happy woman,” Evelynn whispered, staring at his ass.

“Uhh, they fit good. Can we get both of these?” he asked, gesturing to the other pair in the change room. They were two of the more expensive pairs in the store, but Evelynn  _ had  _ said…

“Yes! Of course!” Evelynn all but shouted in her enthusiasm. ‘“I’ll meet you at the till.”

Casper closed the door again, changed back into his regular pants, and came back out. He brought the clothes to the till where the cashier who’d smiled at him was waiting. She scanned the items, and then looked up past Casper, and smiled.

“Hey, Eve. New boy’s a bit younger than your normal ones, huh?”

“No comment, Misuzu,” Evelynn snickered, appearing next to Casper and placing a small bundle of things on the counter next to his new latex pants. Casper looked at it, and blushed crimson. It was a set of small buttplugs in ascending sizes and a good-sized bottle of lube. He looked over at Evelynn with a frown as she handed her credit card to Misuzu. As she handed it over, she slowly turned her head to look Casper in the eyes with a tiny, almost unreadable smile. He wanted to complain about how inappropriate this was, but he didn’t want to throw a fuss or let it be known that he was here with his mother in front of the cashier, either, especially since the two of them apparently knew each other. He remained silent, blushing furiously, and Evelynn just winked at him and then completed the transaction as their purchases were bagged up/

“Mommyyyy,” Casper whined as they got clear of the store. “I really didn’t… I don’t need you to buy me…”

“I don’t know what you’re talking about, baby, I bought these for myself. I date people sometimes, and they all have butts.” Evelynn responded, sounding completely insincere. “Sure, I’m going to leave them unattended on my coffee table where any of my guests could take them without my noticing, but I definitely didn’t buy them for you.”

“...Really?” Casper asked dryly as they got into the car.

“Yep!” Evelynn grinned to herself a little bit, smiling at her own cleverness. Casper sighed and shook his head, completely at a loss as to how to react to Evelynn’s parenting. He definitely wasn’t going to take or use the buttplugs. Well... he kind of wanted to, but doing so would be admitting defeat.

As they returned home from their shopping trip laden with bags of clothes and makeup. As he deposited his spoils in his room, he spotted something in the backyard that he’d meant to ask Evelynn about earlier, but never had. He went back out into the living room and found her tapping away at something on her phone.

“So, uhh, Mommy, is that a hot tub in your backyard?” Casper asked, glancing out the window at the large, box-like fixture visible through the kitchen window.    
  
“Sure is. Gosh, a soak does sound nice tonight after all that driving. I’ll go fire it up, It’ll take about half an hour to be ready, sound good?” Evelynn smiled dreamily.

“Sure, I’ll go get changed,”

Casper went back into his room, and immediately realized he didn’t really have swim trunks or anything like it. He had a few pairs of underwear, but several had already been worn and others probably weren’t suited to hot tubbing. He ended up picking the pair that was least likely to allow his dick to flop out, and made a mental note to ask Evelynn if he could do some laundry tomorrow. He ended up answering texts for several minutes, a few of his friends from Portland were wondering where he was so he took his time answering their queries. 

After finishing up with his messages and social media, he went out to the backyard, sliding the glass door open and stepped out onto the grass. He saw Evelynn was already inside the humming hot tub, facing away from him with her head reclined and her eyes closed. Even over the mechanical whirr of the jets, Casper could hear her humming happily to herself. He climbed up the other side and slowly eased himself into the water.

“Oh, wow,” he murmured, enjoying the embrace of the heated turbulent water. This was the kind of luxury that he’d only really had at public pools and that was a different experience entirely.

“It’s ridiculous how much it costs to maintain this, but it’s one of the few indulgences I splurge on.” Evelynn commented. Casper looked over at her, and jumped a little in surprise. Evelynn was not wearing a bra, the top half of her heavy, round tits were on display above the surface, with her large, dark nipples barely concealed by the translucent water. He was only surprised for about half a second, Evelynn wearing a swimsuit would have been extremely out-of-character, now that he thought about it.

“Very bold choice, wearing tighty whities,” Evelynn winked at him and playfully splashed a bit of water at him, the sudden motion making her tits jiggle.

“You’d rather I be naked, then?” Casper giggled, shielding his face.

“I’m not going to force you, sweetie, but I  _ will _ neg you and imply that you’re a prude and a stick in the mud.” 

“Alright, fine. I can be an inappropriate nudist, too,” Casper stuck his tongue out at her, and then dramatically stood up and stripped out of his underwear, tossing them over the edge. Evelynn immediately stifled a laugh, covering her mouth to keep her snickering under control. Casper looked back at her and scowled, seeing that she was looking at his crotch.

“W-What??” he asked, covering himself with his hands for a moment, and then right after, sitting down. His confidence vanished in a puff of smoke.

“Oh, honey, I’m so sorry, there’s nothing wrong with you, it’s just… well, you clearly didn’t get your size from me.” Though she was apologizing, Evelynn hadn’t stopped smiling and didn’t exactly look remorseful.

“Your… size?” he asked, his defensiveness slightly ebbing away only to be replaced by confusion.

“Oh… you didn’t know?” Evelynn asked. When Casper didn’t respond, she shrugged, and stood up. When her naked breasts came free of the water, Casper glanced away a little bit. He still felt like he could remember them pressing into his back the previous night, but maybe they  _ had  _ just cuddled. When she stood up to her full height, Casper immediately saw what she was referring to. Evelynn didn’t just have a dick, she had a dick that made his look tiny. Heck, her dick made the guys he’d seen in porn look average. It was soft now, hanging low with a gentle curve down between her thighs. Her nutsack looked like more than a handful, the current sizet no doubt assisted by the heat. She was uncut with a decent amount of foreskin bunched up around the tip, but even as he looked, it twitched slightly, a rush of blood hardening it just enough for the foreskin to peel back a bit and reveal the tip of her urethra.

“Uhh… no I… no I didn’t… Mom never mentioned.” Casper blushed bright red at the sight of his Mommy’s cock. It took him a few seconds to tear his gaze away from it, and the realization that he’d been staring a little just made him blush more.

“Well, I’m your biological Mother, you know. Did you assume we’d adopted you or used a sperm donor?” Evelynn remained standing for a few seconds and then eventually, slowly, sat back down, obscuring her cock beneath the translucent water.

“Yeah, I… I guess.” he replied. “Mom never talked about you, and I never thought about it too much.”

“Well, you’re half me and half Cassandra. I was always so proud of you, doctors always said that I’d end up being infertile. I always joked around with Cassie that I’d knock her up just to spite them.

“So, did  _ that _ have anything to do with why the two of you… split up?” Casper asked, gesturing towards Evelynn’s crotch.

Evelynn reacted immediately, her good mood vanishing as though he’d flicked off a light switch. She scowled, not at him, really, but she  _ was  _ looking in his direction. She was quiet for several moments, and Casper shrunk back as the oppressive silence made his skin crawl.

“Cassie said a lot of things to me as we were breaking up.” she said, her voice flat and intense. “A lot of the things she said were about my body, yes. She said them to hurt me, and it did hurt me. I don’t know if it’s part of why we broke up, I couldn’t tell you.”

“I… Mommy, I’m sorry,” Casper murmured.

“Casper, I know I’ve been teasing you a lot this week but I want you to know that your body is beautiful. I just want you to be able to achieve your perfection.”

“Y-Yeah. I know, Mommy. Thanks.” Casper smiled at her. He wasn’t entirely sure what to make of Evelynn’s serious comments, the first serious comments he’d literally ever seen her make. The two of them spent a solid half an hour just sort of relaxing in the hot tub without saying much more to each other.

He floated closer, gave Evelynn a sideways hug, and got out first. She smiled at him and patted him on the cheek. “Sorry to ruin the mood, sweetie. See you tomorrow?” she asked.

“Yeah, see you tomorrow.”

***

Casper woke up, and for a moment, wondered why, since when he opened his eyes, it was pitch black. A moment later, he felt the pressure in his bladder, and he realized that’s what had woken him up. He glanced over at the digital clock next to the bed, and saw that it was 12:30 AM, not even that late. With a grumble, kicked his sheets away and sleepily rose to his feet. He walked into the kitchen, immediately realized that he was going the wrong way, and then pivoted and went towards the upstairs bathroom since the downstairs one didn’t have the heated toilet seat he liked. As he reached the top of the stairs, he heard something. A muffled mumbling and moaning was coming from down the hall. Without thinking the situation through, Casper moved forward curiously, intent on finding out what the sound was. Evelynn’s bedroom door was open, there was the dim light of the bedside lamp on, and she was unmistakably masturbating.

“Mmm, Fuck! Take Mommy’s cum you little tease! Gonna fill your boypussy to bursting. You’re gonna F-Fuck! Fucking leak Mommy’s jizz down your thighs all day you sissy fuckhole!” The words and a whole continuous stream just like them came out of Evelynn’s mouth. She was stroking her cock rapidly, although it looked… no that wasn’t just her cock. She was using the fleshlight he’d seen earlier, and it was making obscene squelching noises as she beat her meat with it. Casper sobered up out of his sleepy state, and silently backed away to use the downstairs bathroom and its stupid cold toilet seat.

“Jeez,” he murmured, shaking his head as he sat down and tried to pee through his half-boner. He tried to erase the image from his mind as he pissed, and he was still very tired so it wasn’t  _ that _ difficult, but… what had she been saying? It was probably all just nonsense sex-talk. Heat of the moment stuff. He finished peeing and wandered back to his room and back to sleep. Best… not to think about it…

***

“Morning, sleepyhead!” Evelynn chimed. Casper was already half-awake, sleepily thumbing through his phone’s notifications under the covers. He yawned and pushed the sheets aside.

“ghwur,” he murmured. 

“What’s that? You wanna be a good boy and come along with Mommy for her run?” Evelynn asked, grinning at him with her hands on her hips.

“Umm? Run?” he asked, the fog clearing a bit.

“Yes! It’s a thing we do where we use our legs to propel us through the hills! It provides us with exercise!” Evelynn plopped down onto the bed and leaned in, kissing him on the forehead and then ruffling his hair until it floofed all over his eyes and he couldn’t see.

“Oh. Oh! Uhh, yeah, sure, why not,” he said, pulling away a little and fixing his hair.

“Yay!” Evelynn kissed him again several times, most of them landing on his cheeks and forehead but one lingered on his mouth and he could have sworn that he felt her slip a little tongue in there, but before he could think too hard about it, she’d bolted back up off the bed and swept out of the room like a hurricane. Casper sat there for a few moments, blinking the sleep out of his eyes, and then went to get changed.

He emerged from his room and found Evelynn in the kitchen eating a bowl of cereal. There was another bowl on the table, and Casper helped himself to it. Evelynn was dressed in a pair of yoga pants and a t-shirt, which was more dressed down than he usually saw her by quite a lot. The pants did absolutely nothing to hide her bulge, and he clearly saw the outline of each of her impressive testicles, and even… no he couldn’t see the veins, that had to be a fold of fabric. When she caught him looking (maybe he was staring a little, if he was being honest,) she silently reached down and grabbed it, giving it a tiny squeeze as she smirked at him.

“S-Sorry. I just… uhhh,” he mumbled around a mouthful of cereal.

“I usually tuck but we’re going for a run so nuts to that. Pun intended.” Casper laughed a little at the awful joke, shaking his head. They finished breakfast, and Evelynn immediately grabbed a little backpack, slipping her arms through the straps. “Onward!” she raised her arm triumphantly, as though the two of them were off to do something glorious. He followed her outside and felt the warm sun contrasted against the cool autumn breeze. 

Evelynn proved to be much more energetic than Casper expected. She set a quick pace, which Casper kept up with at first, but eventually he started to lag behind and Evelynn made a point of circling back around and heckling him teasingly.

“Your Mother is twenty five years older than you and she’s doing circles around you, Casper! Let’s see some hustle!” she shouted in her approximation of a drill sergeant voice.

“I am… not… in… Ahh!” Evelynn slapped his ass, hard, and he stopped and scowled at her.

“Not cool!” he pouted, rubbing the sore handprint.

“Hah! Sorry, couldn’t resist. Take a break?” she did a very poor job of restraining her laughter, but removed her little backpack and withdrew some bottles of water and a little hand towel from it.

“Yeah,” he agreed, taking the bottle of water she held out to him and wandering over to a nearby tree to sit down next to it.

Evelynn sat down next to him and wrapped an arm around his shoulders. She slyly handed him a granola bar like it was contraband, and when he looked over at her, she winked and shushed him. The two of them sat quietly for a while, drinking their water and eating their granola, watching some birds flit from tree to tree.

“Mommy, I’m… I wish I’d gotten a chance to know you before this,” he finally said, enjoying the moment.

“Me too, baby,” Evelynn agreed, giving him an affectionate squeeze.

“I think, uhh… I was thinking about applying at some of the schools up here. Maybe go to one of the Uni’s up here next semester.”

“Shouldn’t be too hard. You have a Canadian citizenship, after all.” Evelynn remarked.

“...I do?” he asked.

“Yeah, of course, you have one Canadian and one American Mother, that’s a pretty common case for dual-citizenship.”

“Oh. I hadn’t thought about that.”

Evelynn chuckled and booped his nose with a finger. “And to answer your question, silly, yes of course you can stay with me if you end up doing that.”   
  


“..Thanks, Mommy,” Casper giggled, snuggling up against her.

After resting for a bit, the two of them went back down the hill to Evelynn’s house. Casper went in first, huffing and puffing and sweating. Evelynn was definitely glistening a little, but she was nowhere near as beat as Casper was.

“I’m… gonna… shower…” Casper wheezed.

“Go ahead, you know where it is.”

Evelynn’s shower was huge, it was at least sixteen square meters with one long, narrow showerhead that covered the center of the room with warm water. Casper wasn’t sure why one would opt to put this style of shower into a house, but the fact that he could stretch and wander around was a strangely nice little convenience. As he stood under the stream of warm water, his cock throbbed needily and he sighed in frustration. He still didn’t understand why his libido was so on fire these past few days. True, he was a nineteen year old boy and thinking about sex wasn’t uncommon for him, but his body had never been so wantonly and uncontrollably horny even when he didn’t want it to be. He gathered up some soap and started washing his chest, and as he ran his hands across his nipples, an electric tingle made him gasp. He gently squeezed one of his nipples, which seemed more swollen than usual, and moaned softly. His cock twitched at the strange tingling pleasure, his body responding like it had made an amazing discovery. Casper contemplated the phenomena for only a few moments before he brought his other hand up to cup and squeeze his other nipple. He moaned and whimpered gently as he fondled and teased himself, exploring this new sensation.

“F-Fuck… so weird…” he murmured to himself as he continued playing with his chest.

“Someone’s having fun~” Evelynn’s sultry voice came from right next to him, and he jumped in surprise. The sudden motion made him slip a little on the slick tiles, but Evelynn grabbed him to keep him steady. “Oh, sorry! You alright, baby?” she asked, squeezing him close.

“Y-Yeah, I’m…” he trailed off as he felt it. Evelynn’s cock was pressing hard into his ass, and one of her hands was wrapped around his chest, fingers idly resting on one of the nipples he’d just been fondling so passionately. “Mommy, what are you doing in here…” he murmured, disentangling himself from her.

“You didn’t close the door, sweetie. I thought that meant you wouldn’t mind sharing, and I needed a post-run shower, too. Are you alright? I know being open with your body can be a big first step for some people.” Evelynn stepped directly under the stream of water, wetting her hair down. She started running her fingers through it with a happy sigh, and Casper looked away, terribly embarrassed. He thought that he’d closed and locked the door, but clearly not, if Evelynn had just walked in without him hearing the door open.

“S-Sorry… I don’t normally…” he murmured.

“Oh don’t apologize, sweetie. You have a gorgeous body and your sensitive boytitties deserve to be played with.” She flicked her hair backwards out of her face, the water keeping her bangs held back.

“They’re not sensitive… or, boytitties,” he huffed indignantly, looking away.

“Oh?” Evelynn asked. While Casper was looking away, she reached forward, firmly grabbing one of his nipples with thumb and forefinger.

“A-Aah!” Casper yelped, overcome with a shock of pleasure and pain as Evelynn squeezed.

“Yeah, not sensitive at all,” Evelynn cackled, seizing his other nipple in her other hand. She grabbed a handful of the soft flesh of his chest and kneaded them. Casper moaned and whined, his knees buckling a little. He looked desperately into Evelynn’s eyes for mercy, but she looked back at him with a sort of manic glee. “You’re definitely not moaning and panting like a desperate little sissy slut because Mommy’s playing with your poor nipples,” Evelynn husked, taking slow, deliberate steps forward.

“M-Mommy! Evelynn! This is… wrong,” Casper gasped, weakly putting his hands on Evelynn’s arms. He was so horny, so overwhelmed by Evelynn’s expert kneading of his chest, that he didn’t even know how to resist.

“Wrong?” she asked. With a quick motion, she pulled him close, spinning him around so that his back was pressed up against her front. She reached one hand down, and grabbed a handful of his ass, squeezing so hard the fat of his cheeks bulged around her fingers. “There’s nothing wrong about fondling a tight, sweet little body like yours.” He felt the heat of her cock, now swollen with blood. It was wedged in between his ass cheeks, and she gyrated her hips gently, rubbing the meat against him. Casper felt his own cock throb and twitch, he was overwhelmed by the closeness and intimacy of the moment, overwhelmed by Evelynn’s presence and dominance.

“Gods, you have such a glorious, perfectly fuckable little ass, you know that, baby?” Evelynn asked, pulling him closer up against her. “I’m  _ so  _ tempted right now to just bend you over right now and  _ Stuff. You. Full.”  _ She accentuated each word of the end of her sentence by roughly slamming her hips forward into his ass. The simulated fucking made him shiver, hyper-aware of how precariously close her dick was to his hole.

“I can’t…” Casper murmured. His hand went halfway to his cock, but he stopped himself. It had almost happened instinctively, his body felt like it was on fire with lust at that moment.

“...Can’t?” Evelynn asked.” There was something strange about her tone. “The first time I fucked your Mom’s slutty asshole, she complained it would never fit.” She moved quickly, roughly bending Casper over at the waist so that he was forced to steady himself with his hands on the wall of the shower. She pressed two wet fingers against his ass and applied some pressure.

“H-Hey, you’re not…” Casper didn’t believe that she was actually doing it right up until his ass relented to the insistent pressure. There was a tiny pinch of pain as they went inside, and Evelynn wasted no time exploring, rubbing her fingers along the walls of his butt. She curled them downward into a spot that made his body tingle, and he moaned at the strange, alien bloom of pleasure that cut through the faint ache of his hole being stretched.

“Yeah, and then ten minutes after she said it, she made noises just like that,” Evelynn growled softly, her grip on Casper’s nipple tightening. Casper tried to struggle and get away, but Evelynn had leverage on him and the floor was slippery enough that he didn’t think he could kick and thrash without totally falling over. “All week I’ve had to put up with you teasing me.” Casper felt Evelyn’s hot tongue trail along his cheek. “Showing off your hot little fuckable body. You have no idea how much you’ve been working me up.” A sharp, suckling bite to Casper’s neck drew a cry of pain from the boy. He bucked under her, struggling. She moved too quickly, her hand on his nipple going up to entwine in his wet hair. She pinned his face against the warm shower tiles until his skull ached under the pressure. “I think it’s time,” her sultry purr tickled his ear. “I’ve been patient enough with you. Let’s see what needy sounds you make when it’s Mommy’s cock in your pussy instead of a pair of fingers.”

“W-What?” Casper gasped, cold panic forming a knot in his belly. This wasn’t teasing, she wasn’t just being inappropriate and messing with him. She meant it. “Evelynn, stop, I don’t want—”

Her hand pressing his head to the tiles squeezed, pulling his hair roughly. “Don’t you lie to me, Cassie. You were born for this. If that cunt hadn’t taken you from me...” There was an angry intensity in her voice that frightened him. He squirmed and pulled away, finally managing to loosen her grip on him but slipping as he did. Evelynn’s fingers came out of his ass and her other hand came away from his head but Casper fell on his ass, twisting so that his back was up against the shower wall. Evelynn towered over him, and he shrank away as she once again got close to him.

“That’s good, Cassie. That’s where you belong, on your knees in front of my cock. Why don’t you show Mommy your appreciation and give her a kiss?” Evelynn grabbed her cock and slapped it against Casper’s cheek.

“Stop it!” Casper raised his hands and slapped away Evelynn’s cock. “Fuck, Mom was right, you’re a monster.” He winced, expecting some kind of reprisal, but when none came, he seized the opportunity and scampered away from her a little. He got away from her and rose up to his feet, feeling his heart racing like crazy in his chest. He looked over at Evelynn and she was… frozen. She was staring at where Casper had been when he was pinned against the wall, one of her hands slowly clenching and unclenching. 

“...Cassie…” Evelynn whispered, still staring into space.

Casper decided not to waste the moment, he darted out of the shower, grabbed a towel, and went to his room. He sat on the bed and covering his face with his hands. He didn’t imagine that. He hadn’t imagined that second night, either. Evelynn… she was serious.

A few minutes later, a knock came at the door. “Sweetie? Can I come in so we can talk about this?” Evelynn’s voice came from the other side of the door. Her voice was… not entirely normal, but it seemed to have regained some semblance of its old self. The door wasn’t locked, it didn’t even have a lock. She could just barge in if she wanted to. 

“I… I think I’d be more comfortable if you stayed outside,” Casper replied.

“Alright, well… I’m so sorry, baby, I just… That… what you just saw doesn’t normally happen to me. I’m so sorry…” her voice sounded fragile, broken, defeated. Casper wasn’t sure what to believe, though. Was it a trick? Had Evelynn had an episode of some kind?

“I don’t know if I believe you, Evelynn. I think I should just go home.” Casper spoke quietly, still feeling shaken by the experience.

“I understand. I’ll buy you some bus tickets and we’ll call you a cab to take you to the bus terminal tomorrow morning, okay?” Casper felt a tiny spike of paranoia at her words. That meant he’d have to stay here tonight. Did he trust her that much? Maybe he should just leave now, walk or pay for a cab himself. Maybe just stay at a hotel or something. That frightened him too, though. He didn’t have much money, Cassandra didn’t provide much for him, and he didn’t know the city at all. 

“O-okay,” he acquiesced. Evelynn  _ did  _ seem to be remorseful. He wasn’t about to forgive her for trying to rape him, but… it was just one night.

“I’ll bring you some lunch so you can eat it in there. I’ll give you some space, but I’ll be out here if you want to talk to me.” There was a brief pause, as though she was waiting for an answer. When one didn’t come, her footsteps echoed down the hall as she left. He sat there on the bed, his thoughts still chaotic and fearful, until Evelynn knocked on the door again.

“Food out here for you,” she called through the door, and nothing more. He opened the door after a bit, and she wasn’t there. There was a plate of leftover curry on the floor, and he took it into the room and ate it quietly. He had no idea what any of this meant, what Evelynn was going through or how he was supposed to feel. Maybe she had some kind of disorder or… something. She’d been calling him Cassie, as though he were actually his Mom. Maybe in that moment, she’d been unable to tell them apart? Maybe that was why his parents had truly split up. Maybe Evelynn just needed to be on medication, or to see a counselor, or... As he ran the scenarios through in his head, his vision began to swim, it started to feel like he was floating underwater.

“W-Whuh?” he murmured, feeling everything swirl around him. Before he could really get a grasp of what was happening, he collapsed forward onto the desk, consciousness slipping away from him.

***

Casper woke up, but it wasn’t normal. He felt weak and sluggish, not tired. He was lying on something soft. He struggled to open his eyes, and then he tried to sit up. His arms… his arms they wouldn’t move. He squirmed and rose up, getting into a sitting position. The room he was in was dim, lit by a single, sputtering lightbulb hanging from the ceiling. The walls were cinderblock and there was a hot water heater sitting in the corner, pipes running up into the ceiling. He was lying on a simple mattress covered by a white sheet. It was barely big enough for him to even lie on. He realized a moment later that his arms were tied or bound together behind his back by something. He pulled against them a little, struggling against it. It didn’t feel like ropes or handcuffs it was like… some kind of sleeve? There was something on his neck, too. It was a collar, a big thick one made out of nylon and there was some kind of box on it, held onto the side of his neck.

“E-Evelynn?” he called out, afraid. What had happened? Had she done this? Was he in the basement?

His voice echoed off the walls a little, fading into nothing.

“This is… fucking insane…” he murmured, trying to get onto his feet. He got halfway up when the sleeves binding his arms went tight and he was pulled backwards. He twisted around and saw that there were ropes attaching him to a hook drilled into the stone. Footsteps echoed outside, and his eyes snapped to a heavy metal door on the far wall. With a heavy clank and screech, it opened, and Evelynn stood in the light.

“Morning, sleepyhead~” she said, echoing what she’d said that morning… or yesterday morning? Had it been a full day, already?

“Evelynn this is fucked up, what did you do? What’s going on?” Casper asked, trembling in fear. Evelynn had a cold, angry look in her eyes, and she had a sort of icy stillness to her body language even as she took several slow steps forward.

“I tried to be nice with you, Cassie,” Evelynn said, not answering his question.

“I am NOT Cassan—” Casper gasped as a sharp, stinging pain bloomed from his neck as the collar buzzed. His body tensed up, his breathing halted for just a moment, and his limbs twitched in agony. It stopped just as rapidly as it had started, and Casper moaned in pain.

“Good girls listen when Mommy is talking. Bad girls get shocked.” Her voice had a deathly finality to it. She clearly wasn’t in the mood to argue.

“Ug…” Casper groaned, shuddering. He looked up at Evelynn defiantly, but she had a remote control in her hands, pointed at him, and the threat was very clear. He didn’t say anything again.

“I didn't want to be hard on you, Cassie. You were being a huge  _ fucking  _ tease, but we were having fun. Right up until you…" She scowled, sneering at him, and Casper flinched, anticipating another shock. When he looked back at her, she'd moved closer, and was pulling up the hem of her dress so that her cock could flop free. It was  _ rock  _ hard.

"Now… do what Mommy told you and give her a  _ fucking  _ kiss."


	2. Grounded

With Evelynn’s cock in his face, Casper hesitated. She smelled like spent cum, like she’d been masturbating just before coming to see him. Another bead of precum formed on the tip, and as he hesitated, she took an aggressive step forward, smearing it on his cheek. Annoyed with his hesitation, she grabbed her cock by the base and slapped him with it, a tiny, low growl rumbling in her throat.

Casper leaned forward a little and landed a single, tentative peck on the tip of her glistening cock. He pulled away with a tiny jerk, and a strand of precum connected her cock to his lower lip for a few seconds before it broke. Almost as soon as it broke, Evelynn’s hands roughly grabbed him by the back of the head and she shoved the head of her dick into his mouth. She sighed, her hands grasping his head with a tremor of anticipation. Casper groaned in surprise, too shocked that she’d actually done it to muster any kind of proper resistance. He tried to catch his balance, but his arms were bound behind his back and he wildly flopped around as Evelynn face-fucked him. He moaned in distress as drool started running down his face. A bit of spittle went flying from the force of one of her hip thrusts, and it got into his eye. She thrust deeply into his mouth, her cock pushing into his gag reflex, making him retch. Soon after she’d started, her hands didn’t fully catch him on a backstroke. Her cock flopped free of his mouth, and he gasped for breath, dark spots forming on his vision. He dry heaved, feeling like he would have vomited if there was anything in his stomach.

He blinked, coughing softly as he tried to get back up. His ears were ringing and he heard a wet, rhythmic sound. His vision cleared up and he saw Evelynn jerking herself off right in his face, moaning in passion. Her moans were feminine but deep and throaty. The passion in them made a shiver run down his spine and a strange thought floated across his mind. Evelynn sounded… really pretty?

Her cum hit him in the face, a spurt hitting him right in his open mouth and he recoiled instinctively. He closed his mouth and tried to flinch away but it was pointless, Evelynn held his head tightly in her other hand and shot rope after rope of cum onto his face until he had to close his eyes. He could taste the slightly bitter tang of Evelynn’s cum on his tongue, and he thought for a moment to spit it out, but that would involve opening his mouth. Instead he left it there and it slowly slid down the back of his tongue towards his throat.

Evelynn sighed happily and gave her cock a quick shake, flinging a few droplets of cum onto Casper’s face. He opened one eyelid and saw her take a step back, her cock slowly softening between her legs, a tiny strand of leftover cum inching down between her knees on a quest to reach the floor.

“Open your mouth,” Evelynn commanded sternly, her mood still dour even in orgasmic afterglow. Casper cracked his eyes open a little wider and looked up at her. When he didn’t open his mouth, she scowled, and grabbed the remote for the shock collar out of her pocket. “Cassie.” she warned.

With reluctance and fear, Casper opened his mouth, and Evelynn smiled cruelly as she worked her mouth a little, and then spat. Her aim was perfect, and it landed right in the back of Casper’s mouth. He jumped a little, more surprised than grossed out. That wasn’t even… he had no idea why anybody would ever even do that. A moment later, he was grossed out, and coughed, trying to dislodge the bit that had already trickled down his throat. Drool ran out of his mouth and he coughed up a bit of spit and cum and phlegm onto the mattress. He heard the door clank, and he looked up to see Evelynn vanishing behind it as it closed.

“H-Hey! Wait!” he croaked, straining against the ropes holding him in place, but the door slammed shut and the lock’s heavy, metallic scraping mocked him and his entrapment. Casper sighed and flopped down on the mattress. He still felt dizzy, tired and woozy. Whatever drugs Evelynn had used to knock him out were still clearly in his system, affecting him. Morbid thoughts crept through his muddy brain like predatory reptiles in a swamp. Evelynn was going to kill him, or cut out his tongue, or skin him alive, or… He was too groggy to properly feel the anxiety and terror the thoughts demanded, but he wasn’t able to dismiss them as unfounded hyperbole, either. He dozed somewhere between wakefulness, sleep, and unconsciousness. It felt like he was drowning, he’d dived off the sinking ship that was his relationship with his Mom and hadn’t reached shore before his strength gave out.

**  
** The door opened again, and Casper shot up, realizing that at one point he’d fallen asleep. He hoped for an instant that maybe it was his Mom or the police or something. It was Evelynn again, of course, but as she walked into the room humming happily to herself, Casper noticed the difference immediately.

“Aww, look at Mommy’s little cum dump. Here, let me clean you up, baby,” Evelynn cooed, kneeling down next to Casper with a damp cloth. Casper winced, expecting some kind of trick or torment, but instead Evelynn just gently started to wipe the dried cum off his face. He wondered if maybe she’d snapped out of it, if the other woman who’d just come and jerked off on his face was gone.

“E-Evelynn, are you—”

“Ah ah,” Evelynn shushed him with a finger on his lips as she finished and put the cloth away. “I’m sorry for being so hard on you, Cassie. I should have set some ground rules from the very start, but I’m still kinda getting the hang of this mothering thing. I’m at a bit of a disadvantage since that spiteful cunt stole you from me, I’ve got seventeen years of parenting to catch up on!” Evelynn giggled and smiled at him warmly.

“It’s okay, Evelynn, just… just let me go…” Casper whined.

“Aww, sorry honey, I can’t do that, you’re grounded. I can’t just let you totally off the hook for being such a bad girl just because I over-reacted a little. But! I want to be fair, so I’ll give you a chance to get your upstairs privileges returned to you.” Casper shook his head, despair clutching at him again. Evelynn  _ was  _ back to her normal self, but clearly happy, sweet Evelynn was every bit as intent on keeping him here as cruel, spit in his mouth Evelynn was.

With a flourish, Evelynn reached into a little handbag she’d brought with her and withdrew a tiny little object that she held out towards him. Casper squinted at it in the dim light… it was… a lipstick tube? Evelynn giggled and then placed it on the ground next to the mattress. “So, to get ungrounded this time, young lady, all you need to do is leave lipstick marks on Mommy’s balls when you suck her cock. Now, I know what you’re thinking, but I’ll be paying attention, the marks need to come from your lips, no cheating! And, of course, to be fair...” She then went back into the handbag and took out a huge purple suction cup dildo and stuck it on the ground next to the lipstick tube with a loud  _ schlorp _ . “For practice!”

“Evelynn you—”

“Ah!” she interrupted him again with an upraised finger. “That’s another thing, missy, none of this ‘Evelynn’ business! You refer to yourself by name, as ‘Cassie,’ and I’m ‘Mommy.’ You’re grounded right now for being rude to me in the shower but I still expect you to follow the basic rules of this house, okay?”

Casper swallowed, and let out a resigned exhale. “Mommy… I’m not sure that I’m comfortable with a new name.”

Evelynn sighed, and gave him a patronizing smile. She grabbed a simple plastic stool from the side of the room and moved it next to the bed, then sat down on it. “I guess you don’t really get how this name thing works, huh? Well, that’s alright, I guess I didn’t explain it simply enough for you. The way that sentence  _ should  _ have worked is ‘Mommy, Cassie isn't sure that Cassie is comfortable with a new name.’ Okay? You try it.”

“Uh…” Casper blinked uncomprehendingly at Evelynn. Was she serious? “I…”

Evelynn snickered at him, and gave him a pitying look. “Alright, sweetie, tell you what, I’ll let you practice that one on your own a little bit, and we’ll go on to the next rule, but next time I come down here, every inappropriate ‘I’ or ‘me’ is gonna be a brief shock from your collar, sound good?”

Casper shook his head. That most certainly did not sound good. Evelynn just giggled and winked at him. “Well, the other rules are pretty simple: Don’t be rude. You do your best to do what Mommy tells you. You don’t mention your thieving cunt of a Mother. You  _ always _ swallow Mommy’s cum, and anything else she puts into your mouth. Don’t think I didn’t notice you coughing up my spit!” She held up an extra finger for every rule she cited off, and smiled sweetly at him as she presented the four fingers at him. “There will be more rules once you get yourself ungrounded, but we’ll start with these four. I don’t want to confuse that silly little brain of yours, after all! You understand, sweetie? Hmm, maybe I should laminate you out a little rule sheet or something…”

Casper swallowed his nervousness, looked up at Evelynn and spoke with a tiny, broken voice. “Cassie understands, Mommy.”

“Aww, what a good girl I have~” Evelynn crooned, leaning in and cradling Casper’s face. Her lips met his, and Casper squeaked a little in surprise, but Evelynn kissed him gently, tenderly, as though they were lovers and not parent and child. Her tongue brushed against his lips, and Casper whined but didn’t snap at her. He knew how futile that would be, and Evelynn kissing him was decidedly less unpleasant than her facefucking him. He let her slip her tongue into his mouth, and she moaned softly, passionately. Evelynn leaned forward, pressing her weight into him as her tongue aggressively explored his mouth.

“Ooh, gosh,” Evelynn gasped softly, breaking the kiss and pulling back a little. She beamed at Casper, a look of pure adoration and joy on her face as she stroked his cheek. “Mommy’s sooo lucky to have such a beautiful little fuck doll. I almost want to fuck that pretty little mouth of yours right now but I’m going to wait until after dinner. Tell you what, why don’t we practice your swallowing since you struggled with it earlier?” Evelynn’s eyes lit up with enthusiasm, and she worked her mouth a little bit, clearly building up some spit.

“N-No that’s fine, I- err, Cassie doesn’t need to…” Casper murmured pulling away a little.

“Aww, Cassie, sweetie, Mommy knows you’re still learning your place but if you can’t handle my spit then how are you going to drink my cum? If I need my fuckdoll to be my urinal, how are you going to handle that? If Mommy gets her girlfriend to give her a nice messy creampie, how are you going to eat that out of her ass? No, it just won’t do, we have to start your training, baby, so, open your mouth, c’mon.” Evelynn sighed wistfully, and then looked at him with a happy smile.

Casper swallowed nervously, biting his lip. Evelynn raised an eyebrow, a gesture laden with implied consequences. He finally opened his mouth a little.

Evelynn sighed, and stuck two fingers in his mouth to pry it open a bit more "This is for your own good, Cassie. Mommy expects to be able to shove you to your knees and use your mouth anywhere, anyplace, anytime. If you can't handle that and spill on the floor, well…" She shook her head, dispelling the implied consequence of her hypothetical scenario. She smiled, pursed her lips, and pushed a large bead of saliva out of her mouth onto them, poising it to drip down into Casper's mouth. She pried his lips a tiny bit further apart, and let it fall, landing on his tongue. Casper shuddered a bit, and swallowed it instantly. It wasn’t that hard, it was only spit after all, but it was kinda gross and he swore he could feel it sticking to the back of his throat even though he knew it was just his imagination.

“Aww, what a good girl,” Evelynn crooned, rubbing Casper’s cheek affectionately. She put her hand on the back of Casper’s neck and pushed him forward. He yelped a little in surprise, not sure what she was doing, but then he felt her tugging at the ropes keeping the armbinder secured to the wall. With a few deft tugs, the rope came free, and Evelynn hummed to herself as she wound the shiny red rope around her hands into a neat little bundle. Casper considered running then and there, but even if the door wasn’t locked, he’d never get it open with his arms restrained as they were.

“Mommy… can I get the armbinder off, too?” Casper asked. Evelynn ignored him completely, still fiddling with her rope. A moment later, he realized why she was ignoring him. “Can… Cassie get Cassie’s armbinder off?” he rephrased his question and rose to his feet to stretch his legs a little.

Evelynn looked at him as if hearing him for the first time and pursed her lips thoughtfully. “Gosh, why would we let you out? My little girl is all cute and helpless and I could just—” Evelynn grabbed Casper and spun him. He instinctively tried to throw his arms out to regain his balance, but instead all he did was… nothing. He was spun around, Evelynn caught him, and pushed him so that he bent at the waist. She slammed her hips forward, rapidly humping him four times.

“Oooh! Fuck! Take Mommy’s cum you dumb sissy cunt!” Evelynn moaned theatrically, panting and breathing heavily, and then moaning loudly as though she were actually orgasming. “Unf!!” she groaned, slamming her hips into his ass with all her strength, and then let him go. He fell face-first onto the bed, blushing profusely as Evelynn snickered at him.

“I can just do that, whenever I feel like it! Nah, that’s too fun, the armbinder stays. Don’t you lie to me Cassie I know a cock-hungry slut like you loves that idea.” She knelt on the bed and turned him over. She swiped her thumb over the head on his cock and then stuck the finger in his mouth. He tasted his own precum, and he met her eyes fearfully. She grinned at him, but the look was laden with expectation.

“Cassie, Mommy doesn’t want to have to repeat this lesson again today.” she said coldly. Casper sucked gently on her finger, cleaning it, and Evelynn’s smile wasn’t motherly, but victorious. “Good. Now, the bathroom is through that door. You’re gonna stay here and think about what you did. I’ll be down in a few hours for my after-dinner blowjob and I’ll bring your dinner with me. If you want to get ungrounded, I suggest you start practicing your deepthroating, missy.” With a smile, she blew him a kiss and left the room. The heavy metal door clanked shut behind her, filling him with a sense of trapped powerlessness.

“Alright, Cassi—Casper. Alright, Casper, let’s find a way out of this nightmare.” he murmured to himself, awkwardly rising up to his feet. The room he was in was all rough cinder block with metal pipes and wooden beams running along the ceiling. The hot water tank looked new, it was bolted into place and it didn’t creak or groan like the tank at his old house. He looked around for something that was sticking out, maybe a sharp metal bit that he could use to cut through the armbinder, but there was nothing, it was all clean, smooth welds and connections. There was a door next to the tank that was heavy, metallic, and had a keyhole to indicate that it was locked. He tried the knob anyway, turning around so that he could fiddle with it with his bound hands, but it didn’t budge. Locked.

The adjoining bathroom had no door, and no lights. He could only make out the dim shape of a sink and a toilet from the light streaming in from the main room. He’d been hoping for a normal toilet with a tank that he could maybe take the lid off of and get a pin or a chain or… something. Instead, this looked like a prison toilet, there was nothing but the bowl, a seat, and a button to flush. The sink, similarly, just had a single button on it, no knobs he could screw off, nothing. Casper awkwardly turned around and used his bound hands to press the button. It clicked, and water started to shoot out of a hole in the sink, more like a water fountain than an actual bathroom sink. It went for about thirty seconds before it clicked off and stopped. He had to turn around and hit the button again so that he could lean down and get some water to drink.

He spent over an hour scouring every nook and cranny of the place. It was clearly designed with keeping people down here in mind. This wasn’t a normal basement that she’d used to throw him down here in a panic, she’d prepared this ahead of time. Was he the first person she’d kept here, or just the latest in a long parade of abductions? The big padlock on the door on the living room, that had to be the door that led down here, this place was all very deliberately designed. It wasn’t a padded room where he couldn’t even hurt himself if he wanted to, but there weren’t any things he could tamper with or break either. There were no weapons he could get to attack Evelynn with, even if his arms weren’t bound, even if she wasn’t bigger and stronger and faster than him.

He went back to the mattress and sat down. He glanced over at the tube of lipstick and the dildo, and then shook his head. No, he wasn’t that desperate. He could tough it out down here until someone came for him, he didn’t need to resort to playing Evelynn’s games. Although… maybe someone might see him, if he was upstairs? There were windows, phones, computers. Fuck. he couldn’t be thinking about caving in to Evelynn’s demented demands already, could he? He pushed the strategy out of his head and tried to just… lay there for now.

Evelynn came back down in what might have been a few hours, but he couldn’t really tell. Her happy demeanor had vanished, but she wasn’t angry and cold like she’d been before either. Without saying a word to him, she pushed him to his knees and shoved her cock into his face. When he was too slow to open his mouth, she shocked him with the collar. The sharp, intense pain made him cry out and tears came to his eyes. An instant later, her cock was in his mouth, and she was fucking his face with shallow thrusts and soft, low grunts.

“Watch the teeth,” Evelynn murmured offhandedly. The words barely registered in Casper’s dazed mind, and when he didn’t acquiesce to her demand, she withdrew her cock, shocked him again, and then stuck her cock right back into his mouth. The gesture had a sort of callous roughness to it, like she had just banged on the side of a monitor to try to get her computer to work. She came in his mouth before long, her cock throbbing and pumping her hot, thick cum into his stomach. He coughed and moaned softly, swallowing her cum as best he could, with only a few small trickles running down his chin. She left just as abruptly as she’d come, and it was only after she’d locked the door again that he saw a little plastic container on the floor.

With some difficulty, he pried the container open with his teeth, revealing some mashed potatoes and chopped carrots. The food was boring, but he ate it and licked the sides of the container clean to sate his hunger.

He slept on the tiny mattress as best he could, but this time, he managed to stay asleep.

***

The sound of the basement door woke him up, jolting him with a feeling of pure, momentary terror. It faded quickly as he stood up, leaving instead him with a sense of general dread that provided plenty enough adrenaline to chase away the drowsiness.

“Sleep well?” Evelynn asked cheerfully. There was a moment of silence as Casper didn’t answer, and Evelynn slowly looked at Casper, meeting his eyes with an intense stare.

“Y-Yes, Mommy,” Casper responded, swallowing nervously.

“Well, you slept all afternoon so I’d hope so,” Evelynn giggled, a tone of friendly teasing immediately returning to her voice. That struck Casper. What time was it, actually? Had she checked on him? Were there cameras? There had to be cameras. “I had a long day at work while you got to snooze around here all day, but I still went and brought you a treat~” It was then that Casper noticed that Evelynn had her hand behind her back.

“Umm…” he mumbled. This was almost definitely going to be bad, or gross, or uncomfortably sexual. He also kind of resented that she had implied that he was relaxing down here. He kept his mouth shut though, he was still terrified of her, but good mood Evelynn had consistently been much better to deal with than angry Evelynn. He briefly wondered if she was doing the personality shifts deliberately as a sort of good cop bad cop routine, or if it was just… how she was

With a giggle and a flourish, Evelynn pulled her arm out from behind her back and presented him with two used condoms that were very  _ very _ full of cum. “Thank... you...?” Casper replied, not sure what he was supposed to do with them.

“Aww, you’re welcome, sweetie. Mommy got  _ sooo _ pent up at work thinking of that tight little throat of yours milking her cock. I ended up jerking off at the desk during meetings a few times. It’s a good thing this publishing cycle is dying down, I’ll have lots of free time for you soon, baby.” As she spoke, she pulled out a pin and ripped a hole in one of the condoms. “Open wide, say ‘aaah.’”

Casper’s stomach lurched a little. She wanted him to drink it. Of course she did. He’d drank Evelynn’s cum many times since she’d locked him down here but that had been fresh from the source. Did… that make it better? Was this worse? Did he  _ prefer  _ drinking his Mommy’s hot girl cum straight from the—

Casper’s runaway thoughts were cut short by the shock collar. He yelped as Evelynn scowled at him for the delay. “Cassie, I thought we were making progress. Be a good sissy and open your cum dump of a mouth.” she said coldly, the anger simmering just below the surface. Casper obeyed, opening his mouth wide and sticking out his tongue. Evelynn immediately upended the condom and squeezed out its contents, the thick, lukewarm cum oozing into his mouth and spreading over his tongue. It tasted funny, it had a strange sort of copperyness to it. Had Evelynn drugged the cum? What was she dumping into his mouth?

“Don’t swallow yet,” she instructed him, even as he retched a little bit. She repeated the process with the second condom, and then with a sadistic smirk, pulled out a third and fourth, and dumped them in too, until his mouth was full to the brim with her slimy cum. She put her hand on the bottom of his chin, and pushed, closing his mouth. Casper winced, breathing through his nose as his cheeks puffed out a little to contain the volume of semen that she’d packed in there. “Look at Mommy and smile, baby,” she whispered huskily, a look of sheer dominant joy on her face. Casper met her eyes and slowly, shakily, curled up the edges of his mouth in his best attempt to smile with a mouth full of cum.

“Swallow your present like the cum-hungry sissy whore you are, and just maybe I won’t fill your mouth back up with my piss.”

Casper swallowed the disgusting cocktail of lukewarm jizz, and immediately coughed and retched, feeling like he might throw up.

“Gooood girl,” Evelynn crooned happily. “Bonus points if you can guess which one of those was mine, and what breed the other three were.”

Casper looked at her, shocked. Which was hers?  _ What ‘breed’ _ ? What was that supposed to mean? She didn’t provide him with an answer, she just walked to the bathroom and tossed the used, ripped condoms into the fountain that he drank out of, tainting it with whatever was left in them.

“Well, I guess you won’t need dinner after that, so I’ll just come down for a bedtime blowjob in a few hours, have a good night, Cassie,” Evelynn blew him a kiss and stood up to leave.   
  


“M-Mommy?” Casper called after her without thinking. The second he did think, he cursed himself. Why bother talking to Evelynn like this, it was pointless, and could only make things worse. Still, he’d opened his mouth now, and when Evelynn stopped in the doorway and looked over her shoulder at him, he kept going. “Mommy… are you doing all this because Cassie told you–” He almost used ‘she’ for a moment, but caught himself. “That Cassie was bi?”

“Oh, don’t be ridiculous, Cassie.” Evelynn barked out a short, mocking laugh. “I was always going to do this to you, right from the start, I had a whole plan. Gods, I was so furious with that idiot doctor when he tried to assign you a male gender.”

“...the start? You mean, even as a child?” he asked, the sickening feeling in his stomach deepening, or maybe that was just the cum shifting around.

“Oh Gods, you and that vindictive cunt are both so ridiculous.” Evelynn scowled, a dark look on her face. She continued on in what was actually a very good impression of Cassandra. “You’re going to give Cassie hormones as a child, Eve? You want to make him just like you, Eve? You’re not performing surgery on our child, Eve. Pfft. No, of course not, I was going to groom you over the course of your childhood, puberty blockers at thirteen, hormone replacement at fifteen or sixteen, surgeries around nineteen. You’d have to be a mad scientist to give adult hormones to children, Cassie, don’t be so gullible.”

Casper blinked in confusion. Between the elaborate evil plan and… Surgeries at nineteen? He was nineteen now. Evelynn’s rant was way too much information for him to process all at once. Evelynn scowled at him for a moment, then shook her head. “No, it’s not your fault, Cassie, it’s that cunt’s fault for not educating you properly.” She sighed, deflated a little, and then returned to his mattress and sat down next to him. For a brief moment, Casper felt a tiny flicker of hope that maybe Evelynn was going to snap out of this.

“I’m so sorry it happened this way, Cassie, I love you so much. I want what’s best for you, I want you to be the best person you can be.” She hugged Casper, resting her cheek on his head and rocking the two of them back and forth a little. She sounded so motherly, so sincere, Casper found himself believing her. Well, believing that she had herself convinced, anyway.

“Mommy… How can you say that and then do all this to Cassie… the collar?” Casper asked quietly, hoping to reach some distant part of her.

Evelynn chuckled, continuing the embrace. “Sometimes, Cassie, children don’t understand why parents do what they do. ‘Why can’t I have candy for breakfast? Why can’t we just live at the amusement part? Why do I have to be Mommy’s fuck doll?’” Evelynn chuckled a little bit, and Casper wasn’t sure if she understood the absurdity of the things she’d just contrasted. “It’ll all make sense eventually, Cassie. Trust that Mommy knows what’s best for you, okay?”

Casper murmured some formless words of despair, and hung his head. Evelynn believed all of this, she really did. There was no light at the end of the tunnel with this woman, he just had to get away from her, that was his only recourse. Even as he thought about it, he thought about the shock collar, and about Evelynn. She terrified him, her planning, her devotion to this process, her dominance. In that moment she seemed indomitable to him, a cruel, powerful, insane Goddess.

“Don’t you worry your pretty little head about it, sweetie. You go ahead and focus on your blowjob practice, Mommy’s going to come back down and  _ reaaalllyyy _ give that whore mouth of yours a rough fucking in a few hours, okay?” She said it so cheerfully, like she was offering him a mug of hot chocolate.

“O-Okay, Mommy…” Casper murmured nervously, not sure what else to say.

***

Casper was alone in the dark room for… he wasn’t sure how long. Days? Weeks? He had little naps here and there but never got any decent amount of sleep. He woke up out of one of his little naps, and squirmed as he realized that his cock was throbbing. He was beginning to suspect that Evelynn was putting cialis or something into his food. His libido still had occasional, uncontrollable flare ups and it seemed to correspond to time periods just after he ate the meals Evelynn gave him. He wasn’t sure if he was just noticing it because he had nothing else to think about, and so he had the time to perform careful analytics about when it happened, or if he was going crazy and drowning in paranoia.

Casper scowled at his stupid, probably drug-fuelled boner, and his arms strained a little against the binder. He would have jerked off but his arms were still bound behind his back. Evelynn had only let him out for five minutes to stretch two times. Finally, he looked at the thin, ragged pillow that was a part of his ‘bed’, then to his cock, then back. Casper grabbed the pillow with his teeth, moved it into the middle of the bed, pressed his cock into it, and started grinding. The stimulation wasn’t especially fulfilling and he found his mind wandering, trying to think about things to help get him off. He thought about some of the girls he’d known back in portland,  _ Evelynn’s tits,  _ a cute boy who worked at the coffee shop he often went to,  _ Evelynn’s ass,  _ some various porn videos he’d liked,  _ Evelynn/s cock, Evelynn, Mommy. _

“Fuck off!” he muttered, fighting against the intrusive thoughts as he feebly tried to get himself off. It was too hard, he couldn’t not think about her and also hump this pillow enough to cum. With a resigned sigh, he stopped fighting it, and thought about that time Evelynn had jerked him off, the times she’d grabbed his hips and ground her cock against his ass. The thoughts were simple, tangible, wrong, and perverted, but they worked. He whined in shame as he humped his pillow, pushing himself close to the relief he wanted so badly that he’d sully some of the only bedding he had.

Suddenly, his next thrust into the pillow, the thrust that would have brought him over the edge, went wrong. He missed, he went too high and his cock only got air, and… The fog of lust lifted a little, and he realized something was suspending him off the bed.

“Ah, Ah, Ah…” Evelynn’s voice came from behind him. “What a naughty girl you are, Cassie. I leave you alone for less than a day and I catch you humping your pillow?”

“I-I didn—” a shock interrupted him, making him scream and gasp. He remembered how he was supposed to talk. “C-Cassie didn’t know that he— Aah! Cassie didn’t know that Cassie wasn’t allowed to do this.” It was true, Evelynn had never forbade him to masturbate, but somehow, he’d known she’d disapprove. Evelynn didn’t strike him as a person who was sympathetic to technicalities.

Evelynn pulled him up to his feet. She looked him in the eye, a smile on her face that frightened him. “Cassie you know that you’re not a boy…” she said softly. She raised a hand to his throat and slowly closed her fingers around it. She squeezed once and exhaled, her smile slowly melting like butter on a pan. “You were  _ never _ supposed to be a boy. Your body gave you the wrong hormones, I was going to  _ fix  _ that until she…” Evelynn’s eyes glazed over, she was staring  _ through  _ Casper, her grip subtly tightening until Casper gasped, feeling his air flow deplete.

Evelynn blinked, her eyes focusing and her cheerful smile reappearing in an instant. “Well, what’s done is done, I suppose. The important thing is that Mommy’s here to set you straight now. Well, set you queer now, I guess.” Evelynn giggled at her own joke.

A thought dawned on him. “Mommy… have you…  _ already _ started giving Cassie hormones?” he asked. He hadn’t thought about it during her earlier rant, but now he wondered.

“Well of course, silly. Even in that bottle of water that I gave you on the car ride up here when we first met.” Casper felt a little sick to his stomach. Of course. That was why his chest was so sensitive and his nipples had been so puffy. Evelynn let go of his throat and patted him on the cheek. “You’re a good girl, Cassie, and good girls cum when they get their sissy pussies stuffed full of dick.”

Casper just blinked, unable to properly process anything Evelynn had just said. He was still floored by the revelation that he’d been taking estrogen for over a week. Was it in his food? Had she secretly put a patch on his arm that he couldn’t see because of the armbinders? While he was lost in thought, something freezing cold pressed into his crotch out of the blue, and he shrieked and jumped, trying to get away from it, but he didn’t have the leverage or the freedom of movement to do so. 

“What the fuc—” she shocked him again. Right. No swearing. He looked down and saw that Evelynn had an ice pack pressed hard into his cock and balls. He shivered and whined in misery as she kept it there, humming happily to herself. 

“There we go~” Eve chanted in a sing-song voice, removing the ice pack. Casper’s boner had thoroughly shriveled. She knelt in front of him and gently started to pull on his balls. He looked down and saw that she was pulling them through a metal ring a few inches in diameter. After the balls, she got his shrunken cock through, and then covered his cock with a metal cylinder. The ring and the covering connected together, and she locked them in place with a little key.

“There, no more temptation,” Evelynn giggled, fondling Casper’s caged cock. He felt the fondling, the pressure, but the head of his penis was completely numbed, she may as well have been fondling someone else for all that he felt it. “Now if you want to feel good you’ll have to tempt your Mommy into pounding your pussy until you scream.” Evelynn stepped back and regarded her handiwork, smiling at him. The outline of her cock was visible, and even twitched when he glanced at it, betraying her act of doing this out of a sense of altruism and parental responsibility. She was enjoying this.

Casper sighed, sat back down on the bed and turned away from her. He couldn’t even masturbate without Evelynn manipulating and tormenting him. Getting the better of him. To his surprise, Evelynn didn’t leave him there in his misery, he felt her weight on the bed and then a moment later, she wrapped her soft arms around his shoulders and leaned into him. “Aww, don’t be sad, Cassie,” she whispered in his ear, her breath hot and warm. “Hmm… You haven’t lost your anal virginity yet, right baby?” she asked suddenly, a genuine curiosity in her voice. Her hands traced teasing patterns across Casper’s chest, fingers applying subtle pressure to his sensitive nipples.

“N-No, Mommy. Cassie hasn’t had… that.”

“Mmm,” Evelynn purred, continuing to grope Casper. In spite of himself, he felt his imprisoned cock stir, starting to strain a little against its cage. “Well, Cassie, a girl’s first time should be special, so when you’ve learned your lesson...” She trailed off and planted a trail of kisses along Casper’s neck, making him shiver. There was a hungry purr in her voice, and she started groping Casper’s chest more firmly.

“Mommy will treat her baby girl to a nice, sweet deflowering. Mommy will slowly, tenderly, gently fuck that pretty, perfect pussy of yours. We’ll go as slow as we have to, we’ll get you whining and whimpering and cumming your brains out all over Mommy’s dick if it takes us all night. Oh, and believe me, sweetie, Mommy isn’t made of time and patience. There will be times when I’ll bend you over a chair and slam my cock into you with one thrust. I’ll dump a load of cum into that slutty, gaping ass of yours and leave you weak-legged and dazed in less than two minutes. But, not for your first time. Your first time will be all about you, baby, doesn’t that sound nice?”

Casper squeezed his eyes shut and shook his head. It sounded messed up. It sounded like more of Evelynn’s deluded fantasy world, and certainly not ‘all about him.’ “Y-Yes, Mommy,” he replied, at a loss as to what else he could say or do. What was worse, when Evelynn kissed him on the mouth again and then left him, he thought about what she’d said. About what she’d promised. He didn’t want to, but his mind demanded movement, it needed something to think about, like he was being forced to walk the plank, and Evelynn’s seductive whispers waited ahead of him like shark-infested waters.

He’d often thought about what his first time with anal sex would be like. He’d been worried it would hurt and that it’d ruin what delicate relationship he’d managed to foster with the other person, whomever they ended up being. But, Evelynn was experienced, skilled, and her cock was so powerful and it smelled like… Casper shook his head, trying to dislodge the image of Evelynn’s hard, fat, meaty fuckpole out of his mind but it remained embedded in his imagination like a knife slammed into the trunk of a tree. He tried to convince himself that Evelynn wouldn’t keep her promise. That she’d hurt him for his first time. She’d leave him crying and hurt, and sore. That thought slipped away, crumbled to dust. He didn’t believe it. Mommy was unpredictable, unstable, and deluded, but… somehow he felt like he’d gotten a good enough grasp on her neuroses’ to know that she would at least _ try _ to keep that promise.

He looked over at the dildo and the lipstick on the ground next to his bed, and took a slow, fearful swallow. Maybe… maybe it was time to practice?

***

  
Casper’s vision swam, he took in a deep, shuddering gasp of air but he couldn’t hear his own breath for a moment. He collapsed on the dingy mattress, coughing and sputtering, sucking in deep, sweet lungfuls of oxygen.

“...nt deep on Mommy’s cock today, huh?” Evelynn’s voice faded in as his hearing slowly returned.

Casper groaned in frustration as he buried his face in the disgusting mattress. This whole stupid challenge to get ungrounded was demented. It was a sick, fucked up, impossible game that Evelynn was playing with him. She was gonna keep him down here in this nasty, dark basement forever. He started to cry. Or at least, he was pretty sure he started to cry, his eyes had watered like crazy, and his face was already soaked with precum and saliva.

“Fuck you…” he murmured into the mattress. His arms were sore and stiff, they’d been in the armbinder for… how long had it been? A week? Ten days? He hadn’t cussed Evelynn out in a while, the electric shocks were awful and every time she did it, she either did it worse or his tolerance to it was going down. He braced for the shock, shuddering and trembling in fear.

Evelynn’s fingers tangled in his thick hair and she pulled. Casper whined as she lifted his head up, and then continued the pressure insistently. Eventually, he relented, and let him drag him back up to his knees.

“Now, now, Cassie.” Evelynn had a playful tone in her voice, still. That was odd. Why hadn’t she shocked him? He’d been a bad girl and broken the rules and— “Tell Mommy you’re sorry. It won’t do to get yourself back in trouble right now.

“Why…?” he croaked. And then, a moment later, “...Cassie is sorry, Mommy…”

“Aww,” Evelynn let go of his hair and cupped his cheek for a moment. “Because you’re not grounded anymore, Cassie.”

Casper blinked, and looked up. Evelynn’s cock was slowly starting to soften, and a long unbroken line of cum connected her urethra to the floor. Her balls were hanging low like they normally did, and they bore faint traces of the same bright, sparkly pink lipstick that she’d put on him prior to the blowjob. He stared at the two fat nuts, the ones that had painted his face and throat with thick, sticky cum so many times over the past two weeks. It felt like a trick, one of Evelynn’s many, many mind games. But… that didn’t make sense. This was what he wanted, right?

“Come on, up, up, let’s get you a proper shower, gosh, you’re a mess, you know that, right?” Casper blinked in confusion at that comment. Him being a mess was… her fault, right? She got him up on his feet and turned him around to loosen the straps of the armbinder. When it came off, his arms felt… weird, they were tingly, and light. Casper turned around, flexing his fingers, and looked at Evelynn. She stared at him intently, smiling ever so slightly, like she was waiting for him to do something. When he didn’t, she nodded.

“Come along,” she called in a musical voice, and headed for the door. She unlocked it and led him through into… a sex dungeon. The room was still underground, but it had the look of a well cared-for space. It was clean, and well-lit, with multiple shiny pieces of restraining equipment scattered about. He didn’t even know what most of the stuff was, or how one would go about using it. He hovered in the doorway, trembling a little bit. Was this what she had freed him for?

“This is the play room,” Eve did a little pivot and gestured with an outstretched arm at the room. “Don’t worry, sweetie, we’re not going to be spending any time here today. But trust me, the play room is for fun, if you’re in trouble, it’s the timeout room.” When Casper didn’t come, Evelynn took his hand and led him to a staircase on the other side of the room. He followed her up and into the morning light of Evelynn’s living room. He hadn’t known it was morning, he’d sort of half-imagined that it was night time. Was he really so mixed up?

Evelynn led him to the bathroom, the same bathroom where they’d…

“Take your time, sweetie,” she urged him into the shower. “Don’t worry, your training collar is waterproof. Can’t have you running away on me, after all.” Evelynn winked at him, and Casper just kind of blinked, confused. How would the collar stop him from running away. Running away…? He was… Right, that’s why he wanted to be ungrounded in the first place, wasn’t it? Surely he wasn’t doing this to  _ make Evelynn happy. _

As if she could read his mind, Evelynn chuckled. “The collar has a proximity sensor, silly. Leave the house and, boop,” she made an expanding gesture with her fingers. “It gives you a big dose on the highest setting. That kinda voltage isn’t meant for humans; you won’t get far.” She winked at him as though she’d just let him in on a scandalous secret.

Casper went through the motions of showering, feeling a mix of being somehow not in his own body, and also like he was coming back to it at the same time. The hot water felt amazing, washing off the sweat, dried cum, and various grime and dirt. It felt like he didn’t know what to do with himself, though. The collar scared him. He wasn’t sure if he believed Evelynn’s proximity sensor story, but he didn’t want to risk it. Phones. He could call the police. Evelynn was bound to leave her phone lying around one time and then he could… get stuck on her password screen, of course.

Casper sighed and slumped against the tile wall of the shower with the hot water thrumming against him. He was done showering, but he didn’t want to leave. Somehow, he doubted that would matter. He’d been told to take his time, probably so that he could wallow in hopelessness.

He came out of the shower wrapped in a towel and without much resistance left in him. He didn’t want to fight or try to trick Evelynn or steal her phone from her. He wanted to, but he didn’t think any of them would work, and he was afraid of both the collar and the ‘timeout room.’ Evelynn was nuts, she’d throw him back in there, he knew. Gods, what else would she do to him, he didn’t want to think about it. He heard her in the living room, and slowly, timidly, made his way there.

Evelynn was sitting on the couch, and she looked over her shoulder at him as he stood meekly in the hallway. She beckoned him closer with a single finger, a smile of power and calm authority on her face. Casper swallowed, and his legs took him around the corner of the couch to stand in front of her. Evelynn grabbed the towel by the bottom and tore it away with a single, powerful yank, throwing it onto the floor behind him.

“Kneel for me, Cassie,” Evelynn said, her voice calm and quiet. She stared at him, a look of power and serenity in her eyes. Somehow, Casper knew that she’d wait all day for him to kneel, because she knew that no matter how long it took, he  _ would _ kneel. He knew it too.

He sank to his knees between Evelynn’s legs. She leaned forward and put a hand behind his head, staring into his eyes intently. “My sweet, beautiful girl…” Evelynn purred. She kissed him deeply, pulling him into her so that he had to rest his hands on her thighs for support. Casper moaned softly, feeling himself melting into her as she wrapped an arm around his waist. Evelynn was really good at kissing, and now that kissing her wasn’t as strange or scary as it had been at first, it was just… kind of nice. Evelynn was never mean to him when they kissed, she never shocked him when they kissed, she never called him a brainless cock sleeve when they kissed.

His hand wandered up her thigh and under the hem of her dress. He put his palm over the bulge in her panties and slowly rubbed it. It was soft now, he  _ had _ just given her a really messy blowjob, after all. Still, it twitched slightly at his touch and Evelynn hummed into the kiss. Evelynn wasn’t forcing him to do it, but somehow, he knew it was what she wanted, and he’d done it without thinking.

With a chuckle, Evelynn broke the kiss and pulled away from him. Casper whined a little, and then a moment later, was struck with how messed up this all was. He was going along with this, and worse still was the realization that he knew he’d keep going along with it, this moment of awareness wasn’t going to empower him to resist her. This was no fever dream about to break, it was an inescapable riptide, pulling him into the depths of Evelynn’s deluded fantasy world.

“So,” Evelynn said, as though she’d just reached some kind of conclusion. “Now that you’ve earned your upstairs privilege, we need to talk about how things are run around here. I expect to be able to bend you over anytime, any place, with no warning, and fuck that sweet, tight, pink boypussy of yours raw. To that effect, I want you to wear a buttplug at all times. Sometimes I’ll take that plug out, dump a load of cum into your cunt, and plug you back up, so you’ll have to get used to walking around with an ass full of cum and a big fat butt plug keeping it in place. If I catch you leaking on the floor, we’ll have to go up a size, okay?”

“Y-Yes Mommy…” Casper murmured, feeling the words washing over him like ice. It felt like someone else was saying them, like someone else was submitting to Evelynn’s dark whims. It felt like… like he was being severed from reality.

“Next, you’ll find some makeup and clothes in your room. There won’t be a strict uniform, but you’re going to make yourself look pretty for me every day. That includes heels, a cute outfit, and makeup. If I think you’re slacking consistently, you might end up back in the basement. If you need any new makeup or clothes, there’s a whiteboard in the kitchen for you to write down requests. Unless Mommy tells you otherwise, you’re to stay in your room when not doing chores. I’ve been pretty thorough about the house’s security, but If I catch you wandering around aimlessly, that’s all the excuse I need to put you back in the basement while I double check that security, do you understand?”

“Cassie understands, Mommy,” he intoned obediently.

“Aww, you’ll get the hang of it in no time. Now, run along to your room sweetie, check out your new clothes and makeup. Mommy’s going to save up some cum for that hungry little boypussy of yours. We’ll have our date tomorrow, are you excited?” as she spoke about their ‘date’, Evelynn leaned in. A finger delicately traced circles around one of his nipples as she teased his neck with the tip of her tongue.

Casper felt a shiver run through him, and his cock throbbed in its cage. “C-Cassie is excited, Mommy.”

“Mm, of course you are,” she whispered in his ear, her hands roughly grabbing and kneading his ass. “Now, go to your room before Mommy gets too horny and too impatient to wait.”

“Y-Yes!” Casper bolted up to his feet, and, after a second of looking at Evelynn to make sure she wasn’t going to grab him, he darted off.

His room was still the same it had been the last time he’d been in there, with the exception of a well-furnished makeup station and a closet full of dresses, skirts, and many other things that were much girlier than he’d ever felt bold enough to wear. The computer was curiously still there, but when he went to look at it, he found that the operating system was totally locked out of anything other than playing video files. He didn’t have to look in the folder labelled ‘Cassie’s jilling material’ to know what it would be full of, but he did anyway. It was full of sissy and trans porn as he’d expected, and he gave up on the machine. Evelynn probably had at least one camera in here and the ability to monitor everything that he did on the machine, so he decided not to push his luck. It wouldn’t matter if he managed to thoroughly hack the machine if it wasn’t even connected to the internet.

He sank into the soft blankets and covers of the bed, feeling a strange sense of relief and… joy? There was a little bit of happiness there, because even though this ordeal wasn’t over, he at least got to be comfortable. Plus, he did genuinely like this bed and this room, they were pretty, and it smelled nice in here. He’d deal with Evelynn… later.

***

Casper woke up some time later in the morning. The house was quiet, but warm and pleasant. As he shook the sleep off and got up, he thought about escape, about contacting the outside world, about finding a way out. Most of those thoughts quickly shriveled on the vine and died, but one plan in particular, he clung to. Evelynn’s phone, it might have emergency calls enabled even on the lock screen. If he could get his hands on it, maybe he could put out a 911 call. If he was going to do that, he needed to be patient and careful, play along with Evelynn, lull her into a false sense of security, and snag her phone during a moment of carelessness.

It was with that strategy in mind that he started to pick out an outfit for himself. Well, that, and, dressing up was fun, even if his selection was significantly more feminine than he usually would have gone. For shoes, his choices mostly had heels of varying degrees of obscenity, including several pairs of ballerina heels that had locking straps on them. He picked a pair of pink shoes that only had about a two or three inch heel and set them aside. For clothes, Evelynn had mostly provided him with several maid outfits, and outfits that resembled maid outfits. Clearly, she had a specific vision in mind for how she wanted him to look. He avoided all of those and went for a sort of schoolgirl-looking outfit with a blouse and a skirt. He got it all on pretty easy (he’d picked the outfit in the first place because it looked pretty simple) and wandered over to the makeup table.

Casper had more than a passing acquaintance with makeup but Evelynn had provided him with a  _ full _ setup, more tools than he knew what to do with. He experimented a little bit just for fun, recreating a look he’d often done that was more goth than maid-like, but if Evelynn didn’t like it, he’d… He paused, thinking about that, sighed, and then redid it a little bit to be a bit more subtle and traditionally feminine.

That done, he went to the door and saw a handwritten note taped to it that Evelynn must have left for him while he was sleeping.

_ Cassie, _

_ No chores today! You can start on that tomorrow. _

_ I’ve left you some educational material on _

_ The computer ;) _

_ If you want to get a head start on _

_ Our date, there’s some toys in the chest of drawers. _

_ See you tonight! Can’t wait <3 _

_ -Mommy. _

He tested the door, but it was locked as he’d expected. He glanced over his shoulder at the computer full of ‘educational material’ but he decided he wasn’t bored enough to torment himself by watching porn while wearing a chastity cage. As the hours went by, his gaze turned to the drawer. Eventually, morbid curiosity overtook him and he opened it, not to actually use any of the toys contained within, but just to see what was in there. The drawer was big and the wood scraped against itself under the weight of its contents. The plugs she’d bought him at the adult store that day were there, all neatly lined up at the front from smallest to largest, and then… behind those…

There were plugs and toys made out of hard plastic, firm rubber, shining steel, and realistic squishy silicone. There were plugs as big as his first, slender rods narrower than a pencil, and a terrifyingly realistic looking dildo shaped like a horse cock that was probably made to scale. It was bent in a curve along the outside perimeter of the drawer. Casper stared in horror for a few seconds, and then swiftly closed the drawer, shaking his head. There was no way he was ever going to have his butthole stretched and gaped out so thoroughly that the horse cock would fit inside him. Evelynn wouldn’t… couldn’t… She could, couldn’t she? More than that, she clearly intended to, why else would she leave this in here. Unless it was just to freak him out, which was clearly working.

He turned away, regretting his decision to indulge his curiosity. He sat on the bed for a bit, paced around the little room. Fiddled with the computer some more. Looked out the window. Sat on the bed again. Read Evelynn’s note again. Chores. The letter mentioned chores. Maybe that wouldn’t be so bad… he’d have something to do, he wouldn’t be sitting here with nothing to do but edge himself. Maybe she’d expect him to cook and take care of the plants, and that’d be nice; he liked cooking. Casper found himself sliding off into a strange daydream where he cooked such good meals for Evelynn that she gave up on the whole sex slave thing and made him her personal chef. He cooked meals for her and her friends, catered parties and celebrations for her book releases.

There was a clicking noise from the door. The loud, clear noise made his heart skip a beat, and he jumped, his daydream fading into nothingness. He hadn’t heard a  _ thing _ prior to it, no front door, no footsteps, nothing. Was the room soundproofed? Evelynn appeared in the doorway, the same radiant smile on her face that he’d first seen when he got off the bus. She was wearing a businesslike dress that hugged her curves without showing off even the faintest sign of her dick - clearly she was tucking.

“Awww, look at you, all pretty for me!” Evelynn gushed. “Aw, but you look so bored! Don’t worry Cassie, Mommy’s newest book deal is pretty much all wrapped up now, I’ll be able to stay home for at least a week to keep you company and train you properly.”

Evelynn looked at Casper, and a silence hung in the air for a moment. Her expression didn’t change, but Casper could feel the timer running, the invisible fuse burning low in the air.

“T-That sounds amazing, Mommy. Cassie is… very excited.” Casper swallowed nervously and did his best to smile for his Mommy. The words were hollow, he was scared and anxious. Fear suddenly started bubbling up within him, Mommy was going to be mad that he wasn’t more enthusiastic, she was going to shock him, throw him into the—

“Aww, sweetie,” Evelynn cooed sympathetically, sensing his discomfort. She walked over and sat down on the bed next to him. She wrapped an arm around his shoulders and pulled him close to her, his face pressing against her right boob. “I know you’re nervous, sweetie, but if you’re a good girl, Mommy will be patient with you.”

Casper nodded, trembling. He sniffled a little bit as Evelynn shushed him. Her other hand went under his skirt, rubbing his smooth thigh. She shushed and murmured softly to him even as her hand explored his body, rubbing his thighs for a full minute before she went further, cupping his caged cock and balls gently. Casper sighed disappointedly, as even when Evelynn rubbed her palm over his imprisoned cock, he barely felt anything.

“You a little frustrated there, Cassie? You want Mommy to give you some relief?” Evelynn whispered to him.

“C-Cassie…” he choked on the words. “Cassie  _ is _ frustrated, Mommy…” he relented.

“Alright then, let’s get started. Get on all fours and show Mommy those fat asscheeks of yours.” Evelynn got up and stood in front of him. She wiggled her hips slightly, then reached down and pulled on her underwear, and her cock flopped out of its tucked position, creating a distinct bulge in her dress. “Come on, baby, show Mommy that you mean it.”   
  


Casper eyed Evelynn’s cock nervously for several long moments as it twitched and shifted, still trapped by her tight dress. He tried to convince himself that she wouldn’t just cram her cock into his ass the second he turned around, but he ultimately couldn’t put the worry to bed. No, Mommy promised him that she wouldn’t. She’d go slow, she’d promised. She’d promised.

Casper raised his legs up, and then twisted, getting onto all fours and sticking his butt out towards her. He looked over his shoulder at her, convinced that taking his eyes off her for just those few instants held danger for him. She hadn’t moved even a little bit, and that chipped away at his anxiety. Mommy had promised him.

“Lift that skirt up for me, sweetie,” Evelynn said, her breathing heavy. She kept her arms at her sides, but Casper could see her fingers twitching.

Casper reached backwards, and grabbed the hem of his skirt, pulling it up until it bunched around his hips. He kept watching her nervously, but every moment that she didn’t move to pull out her cock made him feel a little better. Mommy had promised him.

“Take the panties off. Why did I even give you panties? Tsk, tsk, what an oversight. We’ll get rid of those tomorrow.” There was a soft growl in her voice as she chided herself.

Casper ducked his fingers under the waistband of the panties and slowly pulled them down around his knees. The sight of his bare ass seemed to light a fire in Evelynn’s eyes, she stared at it like a starving lioness. She wouldn’t just pounce on him though, she’d promised him.

“Spread your cheeks for me,” she commanded.

He acquiesced, grabbing two thick handfuls of ass fat and pulling them apart for her. He felt a cool breeze on his asshole as it winked at Evelynn. The tension got to him, and he looked away for a second. She wouldn’t just hurt him, she’d promised.

Evelynn moved swiftly, slapping his hands away and placing her own on his asscheeks instead. She spread his cheeks roughly, and something touched his exposed ass, and he cried out in fear. Evelynn’s tongue, not her cock, speared into his rosebud, her mouth wetly and hungrily sucking on his asshole. It felt… nice. Evelynn’s lips were soft and wet. Her tongue teased and probed at his hole delicately but firmly. Casper found himself moaning, and his cock throbbed gently in his cage. He found himself gyrating his hips back and forth in time with Evelynn’s tonguefucking.

“Oooh, fuck,” Evelynn growled, her lips coming off of his asshole with a loud pop. She pressed her face forward, nose going right into his asshole, and inhaled deeply. “Mm, that smell. You know what smell that is, Cassie?” she asked, sliding one finger into Casper’s spit-slicked hole and sawing it in and out.

“N-No, Mommy…” Casper panted softly, his breath catching in his throat. He was so turned on, and he hadn’t eaten or drank anything all day. This feeling wasn’t the cialis that Evelynn kept giving him, this feeling was his body yearning for his Mommy.

“That’s the smell of a bitch’s pussy. That’s not a boy’s ass, that is a  _ Hole. For. My. Cock. _ ” With her free hand, she delivered four alternating slaps, two to each of Casper’s asscheeks. The slaps weren’t love taps, but she didn’t strike him hard enough to sting. Casper groaned and shuddered, first at the four slaps, and then at the second finger Evelynn inserted into his ass.

“This hole is how my sweet little baby girl is gonna cum tonight. We’re gonna give you sissygasm after sissygasm until these wretched little balls of yours are dry.” Evelynn curled her fingers downard, and gently rubbed her fingertips against a sensitive spot inside Casper’s ass. Casper had dwelt on that night when Evelynn had ambushed him in the shower over and over. He’d gone through several irrational phases of blaming her for ruining the fun they’d been having, blaming himself for not locking the door, and blaming Cassandra for not warning him about Evelynn. More recently though, he’d been having intrusive thoughts about the way Mommy’s fingers had felt in his ass.

“Mommmyyy!” Casper wailed as the intense, overwhelming feeling of having his buzzer pressed wracked his body with pleasure. He felt his soft, caged dick throb and pulse in a soft continual pleasure that was so different from when he masturbated by rubbing it.

“Aww, Mommy’s little sissy likes having her bitch spot rubbed, huh?” Evelynn cooed, her fingers rubbing with a perfect, continual pressure that was supernatural in its precision. For all her mania, Evelynn clearly knew  _ exactly _ how to milk a prostate.

“I-I like it, Mommy,” Casper gasped brathlessly. He buried his face in his sheets as tidal waves of anal pleasure bled him dry. Some tiny, distant part of him was mortified that he was saying this, that all it took was a few fingers in his ass to reduce him to the drooling, moaning, girly sissy that Mommy kept telling him that he was. No sooner had the words left his mouth though, that Evelynn’s fingers stopped moving. Casper moaned in wanton frustration, his body addicted to the pleasure, aching for more.

“Who likes it?” Evelynn asked, her three fingers still buried down to the first knuckle in his stretched ass, but perfectly stationary. She didn’t sound angry, but Casper’s errant use of a pronoun had drained the joy out of her voice.

“C-Cassie! Cassie likes it!” Casper blurted out. Evelynn’s fingers started moving again, but painfully slowly. Casper moaned and shuddered at the slight relief, but it wasn’t quite enough and he was trying to hump his prostate against Evelynn’s hand like he was in heat. Somehow, his motions yielded no extra pressure on his prostate, Evelynn moved with him like the seasoned bitch tamer she was, denying him any pleasure that she wasn’t giving him herself.

“What does Cassie like?” Evelynn asked, continuing her slow, teasing torture of Casper’s prostate.

“M-Mommy’s fingers.” Casper answered, but Evelynn didn’t change her pace at all; that wasn’t the answer she wanted. “I-In Cassie’s ass! Cassie likes it in the ass!” he wailed loudly, his volume getting out of control.

Evelynn still kept her slow, torturous, teasing pace, and she tsked softly, her disapproval wounding Casper like a stab to the gut. “Wrong again. Last guess, Cassie. What’s happening right now?”

“C-Cassie likes having… Cassie’s bitch pussy stuffed with... Mommy’s fingers…” The shame of his admission, and the shame of playing Evelynn’s game, were nothing before the demands of his body, his need to be claimed and broken by his maniac of a mother. 

“Oh, my sissy fuckhole likes my fingers, huh? Well, that’s too bad, because Mommy’s arm is getting tired.” Evelynn slipped her pinky finger into Casper’s ass and opened up her hand a little bit, stretching Casper’s ass just a tiny bit more. She withdrew all four fingers an instant later, leaving Casper’s hole stretched but empty. Casper let out a needy, whorish whine, arching his back like a slut begging for dick, but nothing happened, Evelynn said nothing and did nothing. Casper looked back over his shoulders with needy eyes.

Evelynn had her cock in her hand, she was stroking it slowly, teasingly, and watching Casper intently with a tiny, knowing smile on her face. “Use your words, baby, ask Mommy for what you want.” she said, the words as quiet as a knife in the ribs.

Casper swallowed the lump in his throat. He wanted to ask, he didn’t want to ask. He wanted Evelynn to fuck him, he wanted to go home. He wanted to curl up and fall asleep, he wanted to spread his asscheeks for his Mommy.

“It’s okay, sweetie…” Evelynn whispered, placing the head of her cock up against Cassie’s stretched and puckered butthole. She pressed the tiniest little bit of her weight forward, enough to put pressure on his ass and to make her fat cock bend just a little bit, but not enough to penetrate him. “This is why you were born. You can do this.”

_ ‘This is why I was born.’ _

The thought should have horrified him, it did horrify part of him. The horror didn’t give him strength, he didn’t want to fight Evelynn any more, he couldn’t fight her. He wanted to give up, and these were her terms. That wasn’t all of it though, some part of him wanted this, wanted Mommy’s cock. Some part of him believed everything Evelynn was telling him.

“Please, fuck Cassie, Mommy,” Cassie whispered.

“That’s my girl.” Evelynn pressed two fingers into his ass again, this time efficiently and thoroughly smearing a cold, slippery gel into the tight ring of muscle. The motion was quick and efficient, and before he knew it, the head of her cock retook its place. Evelynn began to push steadily and insistently, and it seemed to Casper like her head would pop right into his tight ass, but it didn’t. Evelynn stopped, withdrew, pushed again, and repeated the process with immense patience and discipline. The head of her cock didn’t ‘pop’ into him, it gained its access slowly but inevitably. The heat of his muscles being stretched and pushed beyond what they’d ever been pushed to combined with the overwhelming heat of Evelynn’s fat fuckpole had Cassie panting in exertion and anticipation.

“Like. A. Glove.” Evelynn tittered as the first few inches of her cock slid inside him. She fucked him like that with several shallow strokes, teasing Cassie with the promise of a hard reaming without actually ramming his hole open. She hummed happily to herself, and switched up her angle, thrusting downward, jabbing and rubbing the head of her cock against Cassie’s prostate.

“O-Oh! F-Fuck!” Cassie groaned as his body shuddered. He felt his balls contract, and his cock twitch in its cage as it leaked precum all over the bed.

Evelynn wrapped one of her hands around Cassie’s neck, pulling his head upwards and applying some pressure on his breathing. “Now, now, Cassie, I know you’re excited, Mommy’s about to show you all kinds of new things that you never knew about your slutty body. But, rules are still rules, you need to watch your language. She pushed again, grinding her cock hard against Cassie’s bitch buzzer and driving her thick meat another inch into his overstimulated ass.

Cassie squealed in delight as her Mommy dominated him and claimed his hole. “Sorry, Mommy,” he babbled, not getting the words out right.

“Ooh, that’s alright sweetie. Mommy knows it’s hard for cock-hungry sissy whores to keep their thoughts straight at the best of times, let alone when I’m about to be balls-deep in them. We’re almost there, Cassie, I’m so proud of you.” Evelynn took another moment to start fucking Cassie’s hole with the length she’d already driven into him, again teasing him with a taste of the thorough fucking he was about to recieve. This time, it felt so good that Cassie shuddered and squealed girlishly, the puddle of precum between his knees spreading as the spike of pleasure made his penis spurt more precum impotently into his sheets.

‘“Please, don’t stop…” The words came out of his mouth, and he meant them, he meant them more than anything. He couldn’t believe he was saying them, it was like someone else was saying them for him. He was glad that this person could do what he couldn’t, could beg Mommy for what he needed.

Evelynn’s hands came down on his slender hips, squeezing him firmly. She pushed, slowly, slowly, slowly, and then with force, slapping her hips against Cassie’s ass with a solid  _ smack. _ “Yessssssss. Gods, I’ve waited so long for this, my sweet baby girl. Mommy’s home.”

Evelynn let go of his hips and grabbed a handful of his hair as she twisted her hips, grinding her fat pole against every part of his sensitive insides. Her voice came in a low growl. “My legs are on fire right now, Cassie. I wanna fucking  _ ram _ you until you can’t scream anymore. I wanna empty my balls inside you just like you’re emptying yours on your sheets.” She started to fuck him in slow, steady, meticulous strokes that belied the primal lack of restraint implied in her voice. Evelynn’s words frightened him,  _ she  _ frightened him. The fear stoked his lust in the moment even as her steady thrusts and precise pressure on his prostate made him see stars in a continual state of orgasmic bliss.

“But I’m not going to, because I love you Cassie, I won’t break my promise. I can see you’re feeling soooo good right now. Are you ready for Mommy’s cum, baby? Your pussy feels  _ so _ good that I can cum whenever I want. Just tell me when you’re ready for it.” A low purr rumbled out of her chest as she straightened up, her thrusts pushing Cassie down into his mattress.

Cassie was so lost that she barely realized what Evelynn was saying. The pleasure coming from his abused prostate had flooded his body until he couldn’t think straight, and now, as it continued to crash through him, he was starting to feel his limits, the sheer exhaustion of having every muscle in his body tensing and untensing was starting to push him up against a wall. The pleasure was getting so intense it was becoming painful.

“G-Give…” Cassie grunted, unable to get anything else out.

Evelynn chuckled at that, but didn’t press him for more details. She slammed her cock into him, delivering one, two, three, four, five thrusts with unrestrained fervor. On the final thrust, she let out a deep, guttural, feminine moan as she buried her cock as deep into Cassie’s ass as it would go. Cassie almost screamed in pain, pleasure, and agonizing stimulation as his Mommy came in him. The fiery heat of her cock spreading and diffusing deep into his belly as she shot spurt after spurt of thick, pent-up cum into him.

“Ooooohhhh…” she groaned, her voice also sounding exhausted. The two of them stayed like that for a moment before she slowly fell forward, her weight pinning him to the bed as her dick continued to throb and twitch in his tight asshole. Neither of them said anything for a long while, the room stank of sex and the only audible sound was both of them breathing as though they’d ran a marathon.   
  
“Mm, how did you like that, my sweet little sissy fuckhole? Did Cassie enjoy her first time?” Evelynn asked breathlessly, her weight pressing heavily onto Cassie’s back. Her fat tits squished softly into him, diffusing her weight over a large area.

“It was… nice, Mommy.” Cassie admitted, the warm afterglow of his multiple anal orgasms making him float on a cloud of hormones and endorphins.

“Good… because Mommy’s not done for the night, and I only promised to be gentle with you the first time.” Her hand came down on his ass hard, the slap echoing off the soundproof walls of Cassie’s room. With a grunt, she pushed herself back up and grabbed his hips, roughly grinding her crotch against his ass, her thick, meaty cock still buried deep inside him.

“B-But Mommy, Cassie needs a—”

“Oh, you got what you needed, Cassie.” Evelynn interrupted him with a low, wicked chuckle. “Now it’s Mommy’s turn to get what she wants, and she wants to  _ wreck _ your fuckhole. Hope you’re ready for a long night~”

**Notes for the Chapter:**

> Oh, it's going to get much more fucked up from here on out, I'm afraid.


End file.
